US 2016/0257686 A1Published application

Purinone Derivatives as Tyrosine Kinase Inhibitors

AssigneePrincipia Biopharma Inc.

InventorTimothy D. OWENS

Life of this patent

Estimating the term…

Abstract

The present disclosure provides compounds and pharmaceutically acceptable salts thereof that are tyrosine kinase inhibitors, in particular BLK, BMX, EGFR, HER2, HER4, ITK, TEC, BTK, and TXK and are therefore useful for the treatment of diseases treatable by inhibition of tyrosine kinases such as autoimmune diseases, cancer and inflammatory diseases. Also provided are pharmaceutical compositions containing such compounds and pharmaceutically acceptable salts thereof and processes for preparing such compounds and pharmaceutically acceptable salts thereof.

Claims19

Dependent claims

A compound of Formula (I):

wherein:
L is O, CO, CH2, S, SO, SO2, NR, NRCO, CONR, or NRCONR′, where (each R and R′ is independently hydrogen or alkyl);
Ar is aryl, heteroaryl, cycloalkyl or heterocyclyl;
R1 is hydrogen, alkyl, cyclopropyl, hydroxy, alkoxy, cyano, halo, haloalkyl or haloalkoxy;
R2 is hydrogen, alkyl, alkynyl, cyclopropyl, alkylamino, dialkylamino, alkylthio, alkylsulfonyl, carboxy, alkoxycarbonyl, alkylaminosulfonyl, dialkylaminosulfonyl, —CONH2, alkylaminocarbonyl, dialkylaminocarbonyl, 3-, 4-, or 5-membered heterocylyl, hydroxy, alkoxy, cyano, halo, haloalkyl or haloalkoxy;
R3, R4, and R5 are independently hydrogen, alkyl, hydroxy, alkoxy, halo, haloalkyl, haloalkoxy, carboxy, alkoxycarbonyl, cyano, —CONH2, amino, or monosubstituted or disubstituted amino;
X is alkylene, -alkynylene-NRa—, cycloalkylene, -alkylene-O—, -cycloalkylene-NRa—, (alkylene)-NRa—, -phenylene-NRa— (where each Ra is hydrogen, alkyl or cycloalkyl), or
(where Z is bond or alkylene, and ring A is heterocycloamino optionally substituted with one or two substituents independently selected from alkyl, hydroxy, alkoxy, or fluoro);
Y is —CO— or —SO2—;
Rc is alkyl, haloalkoxy, substituted alkyl, cycloalkyl, 1-(alkyleneRb)-cycloalkan-1-yl (where Rb is amino, alkylamino, dialkylamino, hydroxy, or monocyclic heteroaryl), 1-NRdRecycloalkan-1-yl (where Rd and Re are independently hydrogen, alkyl, or cycloalkyl), or 3 to 6 membered saturated monocyclic heterocyclyl containing one or two heteroatoms selected from N, O, or S and optionally substituted with one or two substituents independently selected from hydroxy, alkoxy, alkyl, fluoro, aminoalkyl, hydroxyalkyl, or alkoxyalkyl;
or a pharmaceutically acceptable salt thereof.

8 more elements

A compound selected from:

(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-3-cyclopropylacrylonitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-3-cyclopropylacrylonitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-3-cyclopropylacrylonitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-3-cyclopropylacrylamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-3-cyclopropylacrylamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-3-cyclopropylacrylonitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-3-cyclopropylacrylonitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-3-cyclopropylacrylonitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-3-cyclopropylacrylonitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-3-cyclopropylacrylamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
3-cyclopropylacrylamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
3-cyclopropyl-N-methylacrylamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4,4-dimethylpent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4,4-dimethylpent-2-enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4,4-dimethylpent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-4,4-dimethylpent-2-enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-4,4-dimethylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4,4-dimethylpent-2-enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4,4-dimethylpent-2-enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-4,4-dimethylpent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4,4-dimethylpent-2-enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-cyano-dimethylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4,4-dimethylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
N,4,4-trimethylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-methylpent-2-enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-4-methylpent-2-enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-4-methylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-methylpent-2-enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-methylpent-2-enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4-methylpent-2-enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-4-methylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-methylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
N,4-dimethylpent-2-enamide;
(RS), (R), or (S)-4-amino-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-
purin-9(8H)-yl)methyl)pyrrolidine-1-carbonyl)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-4-amino-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-
purin-9(8H)-yl)piperidine-1-carbonyl)-4-methylpent-2-enenitrile;
4-amino-2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-4-amino-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-
purin-9(8H)-yl)propan-2-yl)-2-cyano-4-methylpent-2-enamide;
4-amino-N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)cyclohexyl)-2-cyano-4-methylpent-2-enamide;
(RS), (R), or (S)-4-amino-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-
purin-9(8H)-yl)methyl)azetidine-1-carbonyl)-4-methylpent-2-enenitrile;
4-amino-2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-methylpent-2-enenitrile;
4-amino-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)azetidine-1-carbonyl)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-4-amino-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-
purin-9(8H)-yl)pyrrolidine-1-carbonyl)-4-methylpent-2-enenitrile;
4-amino-N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-4-methylpent-2-enamide;
4-amino-N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)ethyl)-2-cyano-4-methylpent-2-enamide;
4-amino-N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)ethyl)-2-cyano-N,4-dimethylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4-ethoxy-4-methylpent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-ethoxy-4-methylpent-2-enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4-ethoxy-4-methylpent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-4-ethoxy-4-methylpent-2-enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-4-ethoxy-4-methylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-ethoxy-4-methylpent-2-enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-ethoxy-4-methylpent-2-enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-4-ethoxy-4-methylpent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4-ethoxy-4-methylpent-2-enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-4-ethoxy-4-methylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-ethoxy-4-methylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-ethoxy-N,4-dimethylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4-(dimethylamino)-4-methylpent-2-
enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-(dimethylamino)-4-methylpent-2-enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4-(dimethylamino)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-4-(dimethylamino)-4-methylpent-2-enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-4-(dimethylamino)-4-methylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-(dimethylamino)-4-methylpent-2-
enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-(dimethylamino)-4-methylpent-2-
enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-4-(dimethylamino)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4-(dimethylamino)-4-methylpent-2-enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-4-(dimethylamino)-4-methylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-(dimethylamino)-4-methylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-(dimethylamino)-N,4-dimethylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4-methyl-4-morpholinopent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-methyl-4-morpholinopent-2-enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4-methyl-4-morpholinopent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-4-methyl-4-morpholinopent-2-enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-4-methyl-4-morpholinopent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-methyl-4-morpholinopent-2-enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-methyl-4-morpholinopent-2-enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-4-methyl-4-morpholinopent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4-methyl-4-morpholinopent-2-enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-4-methyl-4-morpholinopent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-methyl-4-morpholinopent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
N,4-dimethyl-4-morpholinopent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4-methyl-4-(methylamino)pent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-methyl-4-(methylamino)pent-2-enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4-methyl-4-(methylamino)pent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-4-methyl-4-(methylamino)pent-2-enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-4-methyl-4-(methylamino)pent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-methyl-4-(methylamino)pent-2-enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-methyl-4-(methylamino)pent-2-enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-4-methyl-4-(methylamino)pent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4-methyl-4-(methylamino)pent-2-enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-4-methyl-4-(methylamino)pent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-methyl-4-(methylamino)pent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
N,4-dimethyl-4-(methylamino)pent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4-(ethylamino)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-(ethylamino)-4-methylpent-2-enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4-(ethylamino)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-4-(ethylamino)-4-methylpent-2-enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-4-(ethylamino)-4-methylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-(ethylamino)-4-methylpent-2-enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-(ethylamino)-4-methylpent-2-enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-4-(ethylamino)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4-(ethylamino)-4-methylpent-2-enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-4-(ethylamino)-4-methylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-(ethylamino)-4-methylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-(ethylamino)-N,4-dimethylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4-methyl-4-(methyl(oxetan-3-
yl)amino)pent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-methyl-4-(methyl(oxetan-3-yl)amino)pent-2-
enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4-methyl-4-(methyl(oxetan-3-yl)amino)pent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-4-methyl-4-(methyl(oxetan-3-yl)amino)pent-2-
enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-4-methyl-4-(methyl(oxetan-3-yl)amino)pent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-methyl-4-(methyl(oxetan-3-yl)amino)pent-
2-enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-methyl-4-(methyl(oxetan-3-yl)amino)pent-
2-enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
(carbonyl)-4-methyl-4-(methyl(oxetan-3-yl)amino)pent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4-methyl-4-(methyl(oxetan-3-yl)amino)pent-2-
enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-4-methyl-4-(methyl(oxetan-3-yl)amino)pent-2-
enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-methyl-4-(methyl(oxetan-3-yl)amino)pent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
N,4-dimethyl-4-(methyl(oxetan-3-yl)amino)pent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4-methyl-4-(4-methylpiperazin-1-yl)pent-2-
enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-methyl-4-(4-methylpiperazin-1-yl)pent-2-
enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4-methyl-4-(4-methylpiperazin-1-yl)pent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-4-methyl-4-(4-methylpiperazin-1-yl)pent-2-enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-4-methyl-4-(4-methylpiperazin-1-yl)pent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-methyl-4-(4-methylpiperazin-1-yl)pent-2-
enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-methyl-4-(4-methylpiperazin-1-yl)pent-2-
enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-4-methyl-4-(4-methylpiperazin-1-yl)pent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4-methyl-4-(4-methylpiperazin-1-yl)pent-2-
enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-4-methyl-4-(4-methylpiperazin-1-yl)pent-2-
enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-methyl-4-(4-methylpiperazin-1-yl)pent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
N,4-dimethyl-4-(4-methylpiperazin-1-yl)pent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4-(ethyl(oxetan-3-yl)amino)-4-methylpent-
2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-(ethyl(oxetan-3-yl)amino)-4-methylpent-2-
enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4-(ethyl(oxetan-3-yl)amino)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-4-(ethyl(oxetan-3-yl)amino)-4-methylpent-2-
enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-4-(ethyl(oxetan-3-yl)amino)-4-methylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-(ethyl(oxetan-3-yl)amino)-4-methylpent-2-
enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-(ethyl(oxetan-3-yl)amino)-4-methylpent-2-
enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-4-(ethyl(oxetan-3-yl)amino)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4-(ethyl(oxetan-3-yl)amino)-4-methylpent-2-
enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-4-(ethyl(oxetan-3-yl)amino)-4-methylpent-2-
enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-(ethyl(oxetan-3-yl)amino)-4-methylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-(ethyl(oxetan-3-yl)amino)-N,4-dimethylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4-methyl-4-(2-oxa-6-azaspiro[3.3]heptan-
6-yl)pent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-methyl-4-(2-oxa-6-azaspiro[3.3]heptan-6-yl)pent-
2-enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4-methyl-4-(2-oxa-6-azaspiro[3.3]heptan-6-yl)pent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-4-methyl-4-(2-oxa-6-azaspiro[3.3]heptan-6-yl)pent-
2-enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-4-methyl-4-(2-oxa-6-azaspiro[3.3]heptan-6-yl)pent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-methyl-4-(2-oxa-6-azaspiro[3.3]heptan-6-
yl)pent-2-enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-methyl-4-(2-oxa-6-azaspiro[3.3]heptan-6-
yl)pent-2-enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-4-methyl-4-(2-oxa-6-azaspiro[3.3]heptan-6-yl)pent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4-methyl-4-(2-oxa-6-azaspiro[3.3]heptan-6-
yl)pent-2-enenitrile;;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-4-methyl-4-(2-oxa-6-azaspiro[3.3]heptan-6-yl)pent-
2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-methyl-4-(2-oxa-6-azaspiro[3.3]heptan-6-yl)pent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
N,4-dimethyl-4-(2-oxa-6-azaspiro[3.3]heptan-6-yl)pent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4-methyl-4-(oxetan-3-ylamino)pent-2-
enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-methyl-4-(oxetan-3-ylamino)pent-2-enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4-methyl-4-(oxetan-3-ylamino)pent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-4-methyl-4-(oxetan-3-ylamino)pent-2-enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-4-methyl-4-(oxetan-3-ylamino)pent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-methyl-4-(oxetan-3-ylamino)pent-2-
enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-methyl-4-(oxetan-3-ylamino)pent-2-
enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-4-methyl-4-(oxetan-3-ylamino)pent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4-methyl-4-(oxetan-3-ylamino)pent-2-enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-4-methyl-4-(oxetan-3-ylamino)pent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-methyl-4-(oxetan-3-ylamino)pent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
N,4-dimethyl-4-(oxetan-3-ylamino)pent-2-enamide;
2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4-methyl-4-(piperazin-1-yl)pent-2-
enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-methyl-4-(piperazin-1-yl)pent-2-enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4-methyl-4-(piperazin-1-yl)pent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-4-methyl-4-(piperazin-1-yl)pent-2-enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-4-methyl-4-(piperazin-1-yl)pent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-methyl-4-(piperazin-1-yl)pent-2-enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-methyl-4-(piperazin-1-yl)pent-2-enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-4-methyl-4-(piperazin-1-yl)pent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4-methyl-4-(piperazin-1-yl)pent-2-enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-4-methyl-4-(piperazin-1-yl)pent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-methyl-4-(piperazin-1-yl)pent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
N,4-dimethyl-4-(piperazin-1-yl)pent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-3-(3-methyloxetan-3-yl)acrylonitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-3-(3-methyloxetan-3-yl)acrylonitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-3-(3-methyloxetan-3-yl)acrylonitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-3-(3-methyloxetan-3-yl)acrylamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-3-(3-methyloxetan-3-yl)acrylamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-3-(3-methyloxetan-3-yl)acrylonitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-3-(3-methyloxetan-3-yl)acrylonitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-3-(3-methyloxetan-3-yl)acrylonitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-3-(3-methyloxetan-3-yl)acrylonitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-3-(3-methyloxetan-3-yl)acrylamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
3-(3-methyloxetan-3-yl)acrylamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
N-methyl-3-(3-methyloxetan-3-yl)acrylamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4-methyl-4-(piperidin-1-yl)pent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-methyl-4-(piperidin-1-yl)pent-2-enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4-methyl-4-(piperidin-1-yl)pent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-4-methyl-4-(piperidin-1-yl)pent-2-enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-4-methyl-4-(piperidin-1-yl)pent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-methyl-4-(piperidin-1-yl)pent-2-enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-methyl-4-(piperidin-1-yl)pent-2-enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-4-methyl-4-(piperidin-1-yl)pent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4-methyl-4-(piperidin-1-yl)pent-2-enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-4-methyl-4-(piperidin-1-yl)pent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-methyl-4-(piperidin-1-yl)pent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
N,4-dimethyl-4-(piperidin-1-yl)pent-2-enamide;
(R,S), (R,R), (S,R)or (S,S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-
purin-9(8H)-yl)methyl)pyrrolidine-1-carbonyl)-3-(pyrrolldin-2-yl)acrylonitrile;
(R,S), (R,R), (S,R)or (S,S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-
purin-9(8H)-yl)piperidine-1-carbonyl)-3-(pyrrolidin-2-yl)acrylonitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-3-(pyrrolidin-2-yl)acrylonitrile;
(R,S), (R,R), (S,R)or (S,S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-
purin-9(8H)-yl)propan-2-yl)-2-cyano-3-(pyrrolidin-2-yl)acrylamide;
(RS), (R), or (S)-N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)cyclohexyl)-2-cyano-3-(pyrrolidin-2-yl)acrylamide;
(R,S), (R,R), (S,R)or (S,S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-
purin-9(8H)-yl)methyl)azetidine-1-carbonyl)-3-(pyrrolidin-2-yl)acrylonitrile;
(RS), (R), or (S)-2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-3-(pyrrolidin-2-yl)acrylonitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)azetidine-1-carbonyl)-3-(pyrrolidin-2-yl)acrylonitrile;
(R,S), (R,R), (S,R)or (S,S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-
purin-9(8H)-yl)pyrrolidine-1-carbonyl)-3-(pyrrolidin-2-yl)acrylonitrile;
(RS), (R), or (S)-N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)-2,2-dimethylpropyl)-2-cyano-3-(pyrrolidin-2-yl)acrylamide;
(RS), (R), or (S)-N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)ethyl)-2-cyano-3-(pyrrolidin-2-yl)acrylamide;
(RS), (R), or (S)-N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)ethyl)-2-cyano-N-methyl-3-(pyrrolidin-2-yl)acrylamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4-(cyclopropylamino)-4-methylpent-2-
enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-(cyclopropylamino)-4-methylpent-2-enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4-(cyclopropylamino)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-4-(cyclopropylamino)-4-methylpent-2-enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-4-(cyclopropylamino)-4-methylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-(cyclopropylamino)-4-methylpent-2-
enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-(cyclopropylamino)-4-methylpent-2-
enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-4-(cyclopropylamino)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4-(cyclopropylamino)-4-methylpent-2-enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-4-(cyclopropylamino)-4-methylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-(cyclopropylamino)-4-methylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-(cyclopropylamino)-N,4-dimethylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-3-(1-aminocyclopropyl)acrylonitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-3-(1-aminocyclopropyl)acrylonitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-3-(1-aminocyclopropyl)acrylonitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-3-(1-aminocyclopropyl)-2-cyanoacrylamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-3-
(1-aminocyclopropyl)-2-cyanoacrylamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-3-(1-aminocyclopropyl)acrylonitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-3-(1-aminocyclopropyl)acrylonitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-3-(1-aminocyclopropyl)acrylonitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-3-(1-aminocyclopropyl)acrylonitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-3-(1-aminocyclopropyl)-2-cyanoacrylamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-3-(1-
aminocyclopropyl)-2-cyanoacrylamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-3-(1-
aminocyclopropyl)-2-cyano-N-methylacrylamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4-(azetidin-1-yl)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-(azetidin-1-yl)-4-methylpent-2-enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4-(azetidin-1-yl)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-4-(azetidin-1-yl)-2-cyano-4-methylpent-2-enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-4-
(azetidin-1-yl)-2-cyano-4-methylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-(azetidin-1-yl)-4-methylpent-2-enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-(azetidin-1-yl)-4-methylpent-2-enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-4-(azetidin-1-yl)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4-(azetidin-1-yl)-4-methylpent-2-enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-4-(azetidin-1-yl)-2-cyano-4-methylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-4-
(azetidin-1-yl)-2-cyano-4-methylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-4-
(azetidin-1-yl)-2-cyano-N,4-dimethylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4-methyl-4-(pyrrolidin-1-yl)pent-2-
enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-methyl-4-(pyrrolidin-1-yl)pent-2-enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4-methyl-4-(pyrrolidin-1-yl)pent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-4-methyl-4-(pyrrolidin-1-yl)pent-2-enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-4-methyl-4-(pyrrolidin-1-yl)pent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-methyl-4-(pyrrolidin-1-yl)pent-2-enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-methyl-4-(pyrrolidin-1-yl)pent-2-enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-4-methyl-4-(pyrrolidin-1-yl)pent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4-methyl-4-(pyrrolidin-1-yl)pent-2-enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-4-methyl-4-(pyrrolidin-1-yl)pent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-methyl-4-(pyrrolidin-1-yl)pent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
N,4-dimethyl-4-(pyrrolidin-1-yl)pent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4-(3-hydroxyazetidin-1-yl)-4-methylpent-2-
enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-(3-hydroxyazetidin-1-yl)-4-methylpent-2-
enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4-(3-hydroxyazetidin-1-yl)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-4-(3-hydroxyazetidin-1-yl)-4-methylpent-2-enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-4-(3-hydroxyazetidin-1-yl)-4-methylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-(3-hydroxyazetidin-1-yl)-4-methylpent-2-
enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-(3-hydroxyazetidin-1-yl)-4-methylpent-2-
enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-4-(3-hydroxyazetidin-1-yl)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4-(3-hydroxyazetidin-1-yl)-4-methylpent-2-
enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-4-(3-hydroxyazetidin-1-yl)-4-methylpent-2-
enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-(3-hydroxyazetidin-1-yl)-4-methylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-(3-hydroxyazetidin-1-yl)-N,4-dimethylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4-(4-hydroxypiperidin-1-yl)-4-methylpent-2-
enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-(4-hydroxypiperidin-1-yl)-4-methylpent-2-
enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4-(4-hydroxypiperidin-1-yl)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-4-(4-hydroxypiperidin-1-yl)-4-methylpent-2-
enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-4-(4-hydroxypiperidin-1-yl)-4-methylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-(4-hydroxypiperidin-1-yl)-4-methylpent-2-
enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-(4-hydroxypiperidin-1-yl)-4-methylpent-2-
enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-4-(4-hydroxypiperidin-1-yl)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4-(4-hydroxypiperidin-1-yl)-4-methylpent-2-
enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-4-(4-hydroxypiperidin-1-yl)-4-methylpent-2-
enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-(4-hydroxypiperidin-1-yl)-4-methylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-(4-hydroxypiperidin-1-yl)-N,4-dimethylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-5-hydroxy-4,4-dimethylpent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-5-hydroxy-4,4-dimethylpent-2-enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-5-hydroxy-4,4-dimethylpent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-5-hydroxy-4,4-dimethylpent-2-enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-5-hydroxy-4,4-dimethylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-5-hydroxy-4,4-dimethylpent-2-enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-5-hydroxy-4-dimethylpent-2-enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-5-hydroxy-4,4-dimethylpent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-5-hydroxy-4,4-dimethylpent-2-enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-5-hydroxy-4,4-dimethylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
5-hydroxy-4,4-dimethylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
5-hydroxy-4,4-trimethylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4-(isopropylamino)-4-methylpent-2-
enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-(isopropylamino)-4-methylpent-2-enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4-(isopropylamino)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-4-(isopropylamino)-4-methylpent-2-enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-4-(isopropylamino)-4-methylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-(isopropylamino)-4-methylpent-2-
enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-(isopropylamino)-4-methylpent-2-
enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-4-(isopropylamino)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4-(isopropylamino)-4-methylpent-2-enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-4-(isopropylamino)-4-methylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-(isopropylamino)-4-methylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-(isopropylamino)-N,4-dimethylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4-(4-ethylpiperazin-1-yl)-4-methylpent-2-
enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-(4-ethylpiperazin-1-yl)-4-methylpent-2-enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4-(4-ethylpiperazin-1-yl)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-4-(4-ethylpiperazin-1-yl)-4-methylpent-2-enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-4-(4-ethylpiperazin-1-yl)-4-methylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-(4-ethylpiperazin-1-yl)-4-methylpent-2-
enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-(4-ethylpiperazin-1-yl)-4-methylpent-2-
enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-4-(4-ethylpiperazin-1-yl)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4-(4-ethylpiperazin-1-yl)-4-methylpent-2-enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-4-(4-ethylpiperazin-1-yl)-4-methylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-(4-ethylpiperazin-1-yl)-4-methylpent-2-enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-(4-ethylpiperazin-1-yl)-N,4-dimethylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)pyrrolidine-1-carbonyl)-4-((2-methoxyethyl)amino)-4-methylpent-
2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)piperidine-1-carbonyl)-4-((2-methoxyethyl)amino)-4-methylpent-2-
enenitrile;
2-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)piperidine-1-
carbonyl)-4-((2-methoxyethyl)amino)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-N-(1-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)propan-2-yl)-2-cyano-4-((2-methoxyethyl)amino)-4-methylpent-2-
enamide;
N-(4-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)cyclohexyl)-2-
cyano-4-((2-methoxyethyl)amino)-4-methylpent-2-enamide;
(RS), (R), or (S)-2-(2-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-((2-methoxyethyl)amino)-4-methylpent-2-
enenitrile;
2-(3-((6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)methyl)azetidine-1-carbonyl)-4-((2-methoxyethyl)amino)-4-methylpent-2-
enenitrile;
2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)azetidine-1-
carbonyl)-4-((2-methoxyethyl)amino)-4-methylpent-2-enenitrile;
(RS), (R), or (S)-2-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-
yl)pyrrolidine-1-carbonyl)-4-((2-methoxyethyl)amino)-4-methylpent-2-
enenitrile;
N-(3-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)-2,2-
dimethylpropyl)-2-cyano-4-((2-methoxyethyl)amino)-4-methylpent-2-
enamide;
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-((2-methoxyethyl)amino)-4-methylpent-2-enamide;
and
N-(2-(6-amino-8-oxo-7-(4-phenoxyphenyl)-7H-purin-9(8H)-yl)ethyl)-2-cyano-
4-((2-methoxyethyl)amino)-N,4-dimethylpent-2-enamide;
or a pharmaceutically acceptable salt thereof;
or an (E) or (Z) isomer or a mixture of (E) and (Z) isomer of any of the above compounds.

736 more elements

Dependencies are inferred from the claim text.

Facts

Application: 14/997,248Filed 15 Jan 2016
Priority: 20 Nov 2012
Published: 8 Sep 2016
Term ends: Not estimatedThe source records don’t support an estimate.

Classification15 codes

C07D 473/34
Nitrogen atom: attached in position 6, e.g. adenine
A61K 9/0014
Galenical forms characterised by the site of application: skin, i.e. galenical aspects of topical compositions
A61K 9/0019
Galenical forms characterised by the site of application: injectable compositions; Intramuscular, intravenous, arterial, subcutaneous…
A61K 9/0043
Galenical forms characterised by the site of application: nose

Family

Application61/728,575Us provisional application · filed 20 Nov 2012
Application14/084,519Continuation · filed 19 Nov 2013
Application14/997,248Continuation
US 2014/0142099 A1Published application
US 2016/0257686 A1This patent

From the US filing history. Foreign family members aren’t listed.

Timeline

Citations

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Abstract

Facts

Application

14/997,248Filed 15 Jan 2016

Priority

20 Nov 2012

Published

8 Sep 2016

Term ends

Not estimatedThe source records don’t support an estimate.

Classification15 codes

C07D 473/34
Nitrogen atom: attached in position 6, e.g. adenine
A61K 9/0014
Galenical forms characterised by the site of application: skin, i.e. galenical aspects of topical compositions
A61K 9/0019
Galenical forms characterised by the site of application: injectable compositions; Intramuscular, intravenous, arterial, subcutaneous…
A61K 9/0043
Galenical forms characterised by the site of application: nose