Modulators of Mitotic Kinases

A compound of Formula (I), a prodrug, a polymorph, a tautomer, an enantiomer, a stereoisomer, a solvate, an N-oxide derivative, or a pharmaceutically acceptable salt thereof,

• wherein:
• R1 is hydrogen or halo;
• R2 is -L1-Ra, wherein
• L1 is a bond or alkyl, and
• Ra is cyclohexyl, cycloheptyl, piperidinyl, pyrrolidinyl, furyl, thienyl, morpholinyl, pyridinyl, or pyrimidinyl, each of which is optionally substituted with 1 to 3 substituents;
• or Ra is substituted phenyl;
• R3 is —Rb-L2-K;
• wherein
• Rb is aryl, heteroaryl, cycloalkyl, or heterocycloalkyl, and is optionally substituted with 1 to 3 substituents;
• wherein two of the substituents when adjacent, together with the atom or atoms to which they are attached, can form a 5- to 16-membered ring with 0 to 6 hetero ring atoms,
• L2 is a bond, —(CRxRy)n—, —N═, —O—, —S—, —SO—, SO2, —CO—, —CO—O—, —O—CO—, —NRx—, —NRx—CO—, —NRx—SO2—, —CO—NRx—, —SO2—NRx, —NRx—CO—O—, —NRx—SO2—O—, NRx—CO—NRy—, —NRx—SO2—NRy—, —NRy—, —NRx—CO—CO—O—, —NR—SO2—SO2—O—, —S(O)2—N—CO—R—, —CO—Nx—S(O)2—Ry—, or —(NRxRy)C═N—O—;
• Rc is hydrogen, alkyl, alkenyl, alkynyl, guanidinyl, cycloalkyl, heterocycloalkyl, cycloalkenyl, heterocycloalkenyl, aryl, heteroaryl, (cycloalkyl)alkyl, (heterocycloalkyl)alkyl, (cycloalkenyl)alkyl, (heterocycloalkenyl)alkyl, aralkyl, or heteroaralkyl, and except when being hydrogen, is optionally substituted with 1 to 3 substituents;
• Rx and Ry, are each, independently, -hydrogen, hydroxy, alkyl, alkoxy, amino, —CO-alkyl, —CO-aryl, —SO2-alkyl, —SO2-aryl, —SO2-heteroaryl, or —P(O)(O-alkyl)2, wherein the alkyl or aryl moiety in Rx or Ry is optionally substituted with 1 to 3 substituents;
• wherein each of the 1 to 3 optional substituents on Ra, Rb, Rc, Rx, and Ry, independently, is alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylalkyl, heteroarylalkyl, —OR, —SR, oxo, —C(O)—OR, —C(O)—NRR′, halo, CN, NO2, N3, —C(O)R″, —P(O)(OR)(OR′), —O—P(O)(OR)(OR′), —NR—P(O)(OR)(OR′), —S(O)2—OR, —O—S(O)2—OR, —NR—S(O)2—OR′, —NR—C(O)—OR″, —NR—C(O)—NRR′, —NR—C(S)—NRR′, —C(S)—NRR′, and thioalkyl,
• wherein each of R and R′, independently, is hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, or heteroaralkyl;
• R″ is alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, aralkyl, or heteroaralkyl
• and
• n is 0, 1, 2, or 3.

The compound, wherein said compound is

• N-(4-(1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-N-(methylsulfonyl)methanesulfonamide,
• N-(4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-N-(methylsulfonyl)methanesulfonamide,
• N-(4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)cyclopropanesulfonamide,
• 1-(4-methoxyphenyl)-N-(3-(4-methylpiperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 2-hydroxy-5-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)benzaldehyde,
• ethyl 2-(4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenylamino)-2-oxoacetate,
• N-(2,3,5,6,8,9,11,12,14,15-decahydrobenzo[b]-[1,4,7,10,13,16]hexaoxacyclooctadecin-18-yl)-1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(4-methoxyphenyl)-N-(2,3,5,6,8,9,11,12-octahydrobenzo[b]-[1,4,7,10,13]pentaoxacyclopentadecin-15-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N-(4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-1-(methylsulfonyl)methanesulfonamide,
• 3,3,3-trifluoro-N-(4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)propane-1-sulfonamide,
• (1-10 above)
• 1-(4-methoxyphenyl)-N-(4-morpholinophenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N-(4-(1H-1,2,4-triazol-1-yl)phenyl)-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 2-methoxy-4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenol,
• N-(3,4-dimethoxyphenyl)-1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(3-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)ethanol,
• N1-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)benzene-1,4-diamine,
• N-(4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)methanesulfonamide,
• 4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]primidin-6-ylamino)phenol,
• 1-(4-methoxyphenyl)-N-(3,4,5-trimethoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(4-methoxyphenyl)-N-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• (11-20 above)
• methyl-3-(4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenylamino)-3-oxopropanoate,
• 2-methoxy-N-(4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)acetamide,
• N-(3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 2-ethoxy-5-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenol,
• 2-(4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)ethanol,
• N-(4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)acetamide,
• 2-(2-methoxyethoxy)-N-(4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)acetamide,
• diethyl4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)benzylphosphonate,
• 1-(3-methoxyphenyl)-N-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• dimethyl4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenylphosphoramidate,
• (21-30 above)
• N1-(1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)benzene-1,4-diamine,
• 1-(4-methoxyphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N-(3-methoxyphenyl)-1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 3-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenol,
• 1-(4-methoxyphenyl)-N-(4-(piperidin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N1-bis(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• methyl4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenylcarbamate,
• 2-(4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenylamino)-2-oxoethylacetate,
• N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 2-methoxy-5-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenol,
• (31-40 above)
• 1-(4-methoxyphenyl)-N-(4-(methylthio)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-2-methylphenol,
• 2-methoxy-4-(1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenol,
• N-(3,4-dimethoxyphenyl)-1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 2-(2-methoxyethoxy)-N-(4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]primidin-6-ylamino)phenyl)acetamide,
• (E)-N′-(4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-N,N-dimethylformimidamide,
• 2-methoxy-5-(1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenol,
• N-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)-1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• methyl2-hydroxy-5-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)benzoate,
• 1-(4-methoxyphenyl)-N-(4-(methylsulfonyl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• (41 to 50 above)
• 3-(1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenol,
• 1-(3-methoxyphenyl)-N-(2,3,5,6,8,9,11,12-octahydrobenzo[b]-[1,4,7,10,13]pentaoxacyclopentadecin-15-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N-(benzo[d][1,3]dioxol-5-yl)-1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N-(4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-N-methylmethanesulfonamide,
• 4-methoxy-N-(4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)benzamide,
• N-(2,4-dimethoxyphenyl)-1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(4-methoxyphenyl)-N-(naphthalen-1-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-N-(methylsulfonyl)methanesulfonamide,
• N-(4-(1H-tetrazol-5-yl)phenyl)-1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N,N-dimethyl 4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenylsulfamide,
• (51-60 above)
• N1-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl)benzene-1,4-diamine,
• 3-chloro-N-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]primidin-6-yl)amino)phenyl)propane-1-sulfonamide,
• 3-chloro-N-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-propyl-1,3-sultam,
• 1-cycloheptyl-N-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)benzoicacid,
• 1-cycloheptyl-N-(4-morpholinophenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 3-chloro-N-(3-chloropropylsulfonyl)-N-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)propane-1-sulfonamide,
• (4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)(morpholino)methanone,
• N1-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl)benzene-1,3-diamine,
• 1-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)guanidine,
• (61-70 above)
• N-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)methanesulfonamide,
• dimethyl4-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]primidin-6-ylamino)phenyl)piperazin-1-ylphosphonate,
• (4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)(4-ethylpiperazin-1-yl)methanone,
• 1-cycloheptyl-N-(4-thiomorpholinophenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• dimethyl4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenylphosphoramidate,
• 1-cycloheptyl-N-(4-(piperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-cycloheptyl-N-(4-(1-methyl-1H-tetrazol-5-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 2-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)ethanol,
• 1-allyl-3-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)urea,
• N-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)acetamide,
• (71-80 above)
• 1-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-3-ethyl urea,
• 1-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-3-propylurea,
• 1-cycloheptyl-N-(4-(4-methylpiperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-cycloheptyl-N-(4-(2-methyl-2H-tetrazol-5-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N-(4-(2-(2-chloroethyl)-2H-tetrazol-5-yl)phenyl)-1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)thiophene-2-sulfonamide,
• 4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)benzonitrile,
• N-(3-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-N-(methylsulfonyl)methanesulfonamide,
• 1-cycloheptyl-N-(4-(piperidin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-1-(methylsulfonyl)-N-(methylsulfonylmethylsulfonyl)methanesulfonamide,
• (81-90 above)
• 1-cycloheptyl-N-(4-(2-morpholinoethoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N-(4-(1H-pyrazol-1-yl)phenyl)-1-cycloheptyl-1,1-pyrazolo[3,4-d]pyrimidin-6-amine,
• N-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-N-(phenylsulfonyl)benzenesulfonamide,
• N-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-1,1,1-trifluoro-N-(4-(1,1,1-trifluoro-N-(trifluoromethylsulfonyl)methylsulfonamido)phenyl)methane-sulfonamide,
• N-(benzo[d][1,3]dioxol-5-yl)-1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 2-(4-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)piperazin-1-yl)ethanol,
• 1-cycloheptyl-N-phenyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-cycloheptyl-N-(4-(2-vinyl-2H-tetrazol-5-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• ethyl 4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)benzoate,
• tert-butyl 4-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)piperazine-1-carboxylate,
• (91-100 above)
• N-(4-(1-(4-methoxy-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-N-(methylsulfonyl)methanesulfonamide,
• 1-(4-methoxy-2-methylphenyl)-N-(4-(4-(methylsulfonyl)piperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(4-methoxy-2-methylphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N-(4-(1-(4-methoxy-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)methanesulfonamide,
• 1-(4-methoxy-2-methylphenyl)-N-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(4-methoxy-2-methylphenyl)-N-(4-(trifluoromethoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(4-methoxy-2-methylphenyl)-N-(4-(methylthio)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 2-methoxy-5-(1-(4-methoxy-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenol,
• 3-(6-(4-aminophenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenol,
• 4-(6-(4-aminophenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenol,
• (101-110 above)
• 4-(6-(4-morpholinophenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenol,
• 5-(1-(3-hydroxyphenyl)-1H-pyrazolo[3,4-d]primidin-6-ylamino)-2-methoxyphenol,
• 5-(1-(4-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-2-methoxyphenol,
• N1-(1-(4-iodophenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)benzene-1,4-diamine,
• 4-(4-(6-(4-aminophenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl)but-3-yn-1-ol,
• 4-(4-(6-(3,4-dimethoxyphenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl)but-3-yn-1-ol,
• N-(3,4-dimethoxyphenyl)-1-(4-iodophenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 5-(1-(4-iodophenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-2-methoxyphenol,
• 1-(4-ethylphenyl)-N-(4-(piperidin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(4-iodophenyl)-N-(4-(piperidin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• (111-120 above)
• 1-benzyl-N-(4-(piperidin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(3-methoxybenzyl)-N-(4-(piperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(3,4-dimethoxybenzyl)-N-(4-(piperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• tert-butyl 4-(4-(1-(3,5-dimethoxybenzyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)piperazine-1-carboxylate,
• 1-(3,5-dimethoxybenzyl)-N-(4-(piperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• tert-butyl 4-(4-(3-bromo-1-(3,4-dimethoxybenzyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)piperazine-1-carboxylate,
• tert-butyl 4-(4-(1-(3,4-dimethoxybenzyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)piperazine-1-carboxylate,
• 1-(4-methoxybenzyl)-N-(4-(piperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• tert-butyl 4-(4-(1-(4-methoxybenzyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)piperazine-1-carboxylate,
• (121-130 above)
• ethyl 2-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)acetate,
• 1-cycloheptyl-N-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1h-pyrazolo[3,4-d]pyrimidin-6-amine,
• 2-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)acetic acid,
• 2-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-1-(4-ethylpiperazin-1-yl)ethanone,
• 2-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-N-methylacetamide,
• 2-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-N-isopropylacetamide,
• ethyl 2-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-2-methylpropanoate,
• 2-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-2-methylpropanoic acid,
• ethyl 2-(2-chloro-4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)acetate,
• 2-(2-chloro-4-(1-cycloheptyl-1H-pyrazolo[3,4d]pyrimidin-6-ylamino)phenyl)acetic acid,
• (131-140 above)
• 2-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-2-methyl-1-(4-methylpiperazin-1-yl)propan-1-one,
• 1-cycloheptyl-N-(4-(methylsulfonylmethyl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N-(3-chloro-4-(methylsulfonylmethyl)phenyl)-1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-N-(2-morpholinoethyl)methanesulfonamide,
• N-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]p)pyrimidin-6-ylamino)phenyl)-N-(2-(piperidin-1-yl)ethyl)methanesulfonamide,
• N-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-N-(2-hydroxyethyl)methanesulfonamide,
• N-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-N-isopropylmethanesulfonamide,
• N-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-N-(2-hydroxy-3-(piperidin-1-yl)propyl)methanesulfonamide,
• N-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-N-(2-(pyrrolidin-1-yl)ethyl)methanesulfonamide,
• (141-150 above)
• (S)-N-(4-aminophenethyl)-1-(2,3-dihydro-1H-inden-1-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• (S)-N-(4-(2-(1-(2,3-dihydro-1H-inden-1-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)ethyl)phenyl)-N-(methylsulfonyl)methanesulfonamide,
• N-(4-(1-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-N-(methylsulfonyl)methanesulfonamide,
• 1-butyl-N-(4-(piperidin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-isopropyl-N-(4-(piperidin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(cyclopentylmethyl)-N-(4-(piperidin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• (S)-N-(4-mozpholinophenyl)-1-(1-phenylethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-((6-fluoro-4H-benzo[d][1,3]dioxin-8-yl)methyl)-N-(4-morpholinophenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(furan-2-ylmethyl)-N-(4-(piperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• ethyl2-(6-(4-(piperidin-1-yl)phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetate,
• N-(4-morpholinophenyl)-1-(pyridin-2-ylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-methyl-N-(4-(piperidin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N-(4-morpholinophenyl)-1-(1,2,3,4-tetrahydronaphthalen-1-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(1-benzylpiperidin-4-yl)-N-(4-morpholinophenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine, or
• 1-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-N-(4-morpholinophenyl)-1,1-pyrazolo[3,4-d]pyrimidin-6-amine.

The compound, wherein the compound is

• N-(4-(1H-tetrazol-5-yl)phenyl)-1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N-(4-(1H-tetrazol-5-yl)phenyl)-1-(biphenyl-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N-(4-(1H-tetrazol-5-yl)phenyl)-1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N-(4-(1H-tetrazol-5-yl)phenyl)-1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-cycloheptyl-N-(4-morpholinophenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(biphenyl-2-yl)-N-(4-morpholinophenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N-(4-morpholinophenyl)-1-(phenanthren-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(3-methoxyphenyl)-N-(4-morpholinophenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(4-methoxyphenyl)-N-(4-morpholinophenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-cycloheptyl-N-(4-(piperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(biphenyl-2-yl)-N-(4-(piperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(3-methoxyphenyl)-N-(4-(piperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(4-methoxyphenyl)-N-(4-(piperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)benzoic acid,
• 4-(1-(biphenyl-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)benzoic acid,
• 4-(1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)benzoic acid,
• 4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)benzoic acid,
• N1-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl)benzene-1,4-diamine,
• N1-(1-(biphenyl-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)benzene-1,4-diamine,
• N1-(1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)benzene-1,4-diamine,
• N1-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)benzene-1,4-diamine,
• N-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-N-(methylsulfonyl)methanesulfonamide,
• N-(4-(1-(biphenyl-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-N-(methylsulfonyl)methanesulfonamide,
• N-(4-(1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-N-(methylsulfonyl)methanesulfonamide,
• N-(4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-N-(methylsulfonyl)methanesulfonamide,
• N-(4-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)methanesulfonamide,
• N-(4-(1-(biphenyl-2-yl)-1H-pyrazolo[3,4-d]primidin-6-ylamino)phenyl)methanesulfonamide,
• N-(4-(1-(phenanthren-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)methanesulfonamide,
• N-(4-(1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)methanesulfonamide,
• N-(4-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)methanesulfonamide,
• 1-cycloheptyl-N-(4-(4-methylpiperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(biphenyl-2-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(3-methoxyphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(4-methoxyphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 5-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-2-methoxyphenol,
• 5-(1-(biphenyl-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-2-methoxyphenol,
• 2-methoxy-5-(1-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenol,
• 4-(6-(4-(N-(methylsulfonyl)methylsulfonamido)phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl dihydrogen phosphate
• 4-methoxy-N1-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)benzene-1,3-diamine
• 4-(6-(4-(N-(methylsulfonyl)methylsulfonamido)phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl acetate
• 4-(6-(4-(N-(methylsulfonyl)methylsulfonamido)phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl sulfamate
• N-(4-(1-(4-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-N-methylsulfonyl)methanesulfonamide,
• 2-methoxy-5-(1-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenol,
• 1-(cyclopentylmethyl)-N-(4-(piperidin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• (S)-N-(4-morpholinophenyl)-1-(1-phenylethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-((6-fluoro-4H-benzo[d][1,3]dioxin-8-yl)methyl)-N-(4-morpholinophenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(furan-2-ylmethyl)-N-(4-(piperazin-1-yl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N-(4-morpholinophenyl)-1-(pyridin-2-ylmethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• 1-(1-benzylpiperidin-4-yl)-N-(4-morpholinophenyl)-1H-pyrazolo[3,4-d]primidin-6-amine,
• 1-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-N-(4-morpholinophenyl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine,
• N-(5-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)pyridine-2-yl)-N-(methylsulfonyl)methanesulfonamide,
• N-(5-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)pyridin-2-yl)methanesulfonamide,
• N-(5-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)pyridin-2-yl)-N-(2-hydroxyethyl)methanesulfonamide,
• N-(4-(6-(6-(N-(methylsulfonyl)methylsulfonamido)pyridin-3-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl)-2-(pyrrolidin-1-yl)acetamide,
• N-(4-(6-(6-(methylsulfonamido)pyridin-3-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl)-2-(pyrrolidin-1-yl)acetamide,
• N-(5-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)pyridin-2-yl)-N-(2-morpholinoethyl)methanesulfonamide,
• N-(5-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)pyridin-2-yl)-N-(2,3-dihydroxypropyl)methanesulfonamide,
• N-(4-(6-(6-(N-(2,3-dihydroxypropyl)methylsulfonamido)pyridin-3-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl)-2-(pyrrolidin-1-yl)acetamide,
• tert-butyl 4-(6-(6-(N-(2,3-dihydroxypropyl)methylsulfonamido)pyridin-3-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenylcarbamate,
• tert-butyl 4-(6-(6-(N-(2-morpholinoethyl)methylsulfonamido)pyridin-3-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenylcarbamate,
• N-(5-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)pyrimidin-2-yl)methanesulfonamide,
• N-(5-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)pyrimidin-2-yl)-N-(2,3-dihydroxypropyl)methanesulfonamide,
• tert-butyl sulfonamido)pyrimidin-5-ylamino) 1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenylcarbamate,
• N-(5-(1-cycloheptyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)pyrimidin-2-yl)-N-(2-morpholinoethyl)methanesulfonamide,
• N-(4-(6-(2-(N-(2,3-dihydroxypropyl)methylsulfonamido)pyrimidin-5-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenyl)-2-(pyrrolidin-1-yl)acetamide,
• tert-butyl 4-(6-(2-(N-(2-morpholinoethyl)methylsulfonamido)primidin-5-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)phenylcarbamate,
• tert-butyl 5-(6-(2-(N-(2-morpholinoethyl)methylsulfonamido)pyrimidin-5-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyridin-2-ylcarbamate,
• N-(5-(6-(2-(N-(2,3-dihydroxypropyl)methylsulfonamido)pyrimidin-5-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyridin-2-yl)-2-(pyrrolidin-1-yl)acetamide,
• N-(5-(6-(6-(N-(2,3-dihydroxypropyl)methylsulfonamido)pyridin-3-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyridin-2-yl)-2-(pyrrolidin-1-yl)acetamide,
• tert-butyl 5-(6-(6-(N-(2-morpholinoethyl)methylsulfonamido)pyridin-3-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyridin-2-ylcarbamate,
• tert-butyl 6-(6-(6-(N-(2-morpholinoethyl)methylsulfonamido)pyridin-3-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyridin-3-ylcarbamate,
• N-(6-(6-(6-(N-(2,3-dihydroxypropyl)methylsulfonamido)pyridin-3-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyridin-3-yl)-2-(pyrrolidin-1-yl)acetamide,
• tert-butyl 6-(6-(2-(N-(2,3-dihydroxypropyl)methylsulfonamido)pyrimidin-5-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyridin-3-ylcarbamate,
• tert-butyl 6-(6-(6-(N-(2,3-dihydroxypropyl)methylsulfonamido)pyridin-3-ylamino)-1H-pyrazolo[3,4-d]primidin-1-yl)pyridin-3-ylcarbamate,
• N-(5-(1-(3-hydroxybenzyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)pyridin-2-yl)methanesulfonamide,
• N-(2,3-dihydroxypropyl)-N-(5-(1-(3-hydroxybenzyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)pyridin-2-yl)methanesulfonamide,
• N-(2,3-dihydroxypropyl)-N-(5-(1-((2-hydroxypyridin-4-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)pyridin-2-yl)methanesulfonamide,
• N-(5-(1-(3-hydroxybenzyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)pyridin-2-yl)-N-(2-morpholinoethyl)methanesulfonamide,
• N-(2,3-dihydroxypropyl)-N-(4-(1-((2-hydroxypyridin-4-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)methanesulfonamide, or
• N-(5-(1-((2-hydroxypyridin-4-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)pyridin-2-yl)-N-(2-morpholinoethyl)methanesulfonamide.