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US 11,858,907 B2Granted
Kinase modulators
AssigneeRhizen Pharmaceuticals SA
InventorsMeyyappan Muthuppalaniappan, Srikant Viswanadha, Govindarajulu Babu, Swaroop K. Vakkalanka
Life of this patent
Estimating the term…
Abstract
The present invention provides PI3K protein kinase modulators of Formula (I) wherein R, n, R1, R2, L1, Cy1 and Cy2 are as defined herein, methods of preparing them, pharmaceutical compositions containing them and methods of treatment, prevention and/or amelioration of kinase mediated diseases or disorders with them.
Claims18
A compound of formula
- or a tautomer thereof, N-oxide thereof, pharmaceutically acceptable ester thereof, prodrug thereof, or pharmaceutically acceptable salt thereof, wherein
- each occurrence of R is independently selected from hydrogen, halogen, —ORa, CN, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl, substituted or unsubstituted C2-6 alkynyl, substituted or unsubstituted C3-8 cycloalkyl, and substituted or unsubstituted heterocyclic group;
- R1 and R2 may be the same or different and are independently selected from hydrogen, halogen, and substituted or unsubstituted C1-6 alkyl, or both R1 and R2 directly bound to the carbon atom to which they are attached, may be joined to form a substituted or unsubstituted saturated or unsaturated 3-10 member ring, which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NRa and S;
- Cy1 is a monocyclic group selected from substituted or unsubstituted cycloalkyl, substituted heterocyclic group, substituted or unsubstituted aryl and unsubstituted heteroaryl;
- Cy2 is selected from a substituted heterocyclic group, substituted aryl and substituted or unsubstituted heteroaryl;
- L1 is absent or selected from —(CRaRb)q—, or —C(═Y)—;
- each occurrence of Ra and Rb may be the same or different and are independently selected from hydrogen, halogen, hydroxy, cyano, substituted or unsubstituted (C1-6)alkyl, —NRcRd (wherein Rc and Rd are independently hydrogen, halogen, hydroxy, cyano, substituted or unsubstituted (C1-6)alkyl, and (C1-6)alkoxy) and —ORc (wherein Rc is substituted or unsubstituted (C1-6)alkyl) or Ra and Rb are directly bound to a common atom, they may be joined to form an oxo group (═O) or form a substituted or unsubstituted saturated or unsaturated 3-10 member ring, which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NRd (wherein Rd is hydrogen or substituted or unsubstituted (C1-6)alkyl) or S;
- Y is selected from O, S, and NRa;
- n is an integer from 1 to 4;
- and
- q is 0, 1 or 2.
8 more elements
A compound of the formula:
- or a tautomer thereof, N-oxide thereof, pharmaceutically acceptable ester thereof, prodrug thereof, or pharmaceutically acceptable salt thereof, wherein
- R is selected from hydrogen, halogen, —ORa, CN, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl, substituted or unsubstituted C2-6 alkynyl, substituted or unsubstituted C3-8 cycloalkyl, and substituted or unsubstituted heterocyclic group;
- R1 and R2 may be the same or different and are independently selected from hydrogen, halogen, and substituted or unsubstituted C1-6 alkyl, or both R1 and R2 directly bound to the carbon atom to which they are attached, may be joined to form an oxo group (═O) or a substituted or unsubstituted saturated or unsaturated 3-10 member ring, which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NRa and S;
- Cy1 is a monocyclic group selected from substituted or unsubstituted cycloalkyl, substituted heterocyclic group, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;
- Cy2 is selected from substituted or unsubstituted heterocyclic group and substituted or unsubstituted heteroaryl;
- L1 is absent or selected from —(CRaRb)q—, or —C(═Y)—;
- each occurrence of Ra and Rb may be the same or different and are independently selected from hydrogen, halogen, hydroxy, cyano, substituted or unsubstituted (C1-6)alkyl, —NRcRd (wherein Rc and Rd are independently hydrogen, halogen, hydroxy, cyano, substituted or unsubstituted (C1-6)alkyl, and (C1-6)alkoxy) and —ORc (wherein Rc is substituted or unsubstituted (C1-6)alkyl) or when Ra and Rb are directly bound to a common atom, they may be joined to form an oxo group (═O) or form a substituted or unsubstituted saturated or unsaturated 3-10 member ring, which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NRd (wherein Rd is hydrogen or substituted or unsubstituted (C1-6)alkyl) or S;
- Y is selected from O, S, and NRa;
- and
- q is 0, 1 or 2.
7 more elements
A compound of the formula (IA-I) or (IA-II):
- or a tautomer thereof, N-oxide thereof, pharmaceutically acceptable ester thereof, prodrug thereof, or pharmaceutically acceptable salt thereof, wherein
- each occurrence of R is independently selected from hydrogen, halogen, —ORa, CN, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl, substituted or unsubstituted C2-6 alkynyl, substituted or unsubstituted C3-8 cycloalkyl, and substituted or unsubstituted heterocyclic group;
- R1 and R2 may be the same or different and are independently selected from hydrogen, halogen, and substituted or unsubstituted C1-6 alkyl, or both R1 and R2 directly bound to the carbon atom to which they are attached, may be joined to form an oxo group (═O) or a substituted or unsubstituted saturated or unsaturated 3-10 member ring, which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NRa and S;
- Cy1 is a monocyclic group selected from substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic group, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;
- each occurrence of Ra may be the same or different and are independently selected from hydrogen, halogen, hydroxy, cyano, substituted or unsubstituted (C1-6)alkyl, —NRcRd (wherein Rc and Rd are independently hydrogen, halogen, hydroxy, cyano, substituted or unsubstituted (C1-6)alkyl, and (C1-6)alkoxy) and —ORc(wherein Rc is substituted or unsubstituted (C1-6)alkyl);
- n is an integer from 1 to 4;
- each occurrence of X is independently selected from CR3 or N;
- and
- each occurrence of R3 is independently selected from hydrogen, hydroxy, halogen, carboxyl, cyano, nitro, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkylalkyl, substituted or unsubstituted cycloalkenylalkyl substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted heterocyclic ring, substituted heterocyclylalkyl ring, substituted or unsubstituted guanidine, —COORx, —C(O)Rx, —C(S)Rx, —C(O)NRxRy, —C(O)ONRxRy, —NRyRz, —NRxCONRyRz, —N(Rx)SORy, —N(Rx)SO2Ry, —(═N—N(Rx)Ry), —NRxC(O)ORy, —NRxRy, —NRxC(O)Ry—, —NRxC(S)Ry, —NRxC(S)NRyRz, —SONRxRy—, —SO2NRxRy—, —ORx, —ORxC(O)NRyRz, —ORxC(O)ORy—, —OC(O)Rx, —OC(O)NRxRy, —RxNRyC(O)Rz, —RxORy, —RxC(O)ORy, —RxC(O)NRyRz, —RxC(O)Rx, —RxOC(O)Ry, —SRx, —SORx, —SO2Rx, and —ONO2, wherein Rx, Ry and Rz in each of the above groups can be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkylalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted heterocyclic ring, substituted or unsubstituted heterocyclylalkyl ring, or substituted or unsubstituted amino, or any two of Rx, Ry and Rz may be joined to form a substituted or unsubstituted saturated or unsaturated 3-10 membered ring, which may optionally include heteroatoms which may be the same or different and are selected from O, S, or NRx wherein Rx is hydrogen or substituted or unsubstituted alkyl.
6 more elements
A compound of formula (IA-V)
- or a pharmaceutically acceptable salt thereof,
- wherein
- each occurrence of R is independently selected from hydrogen, halogen, —ORa, CN, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl, substituted or unsubstituted C2-6 alkynyl, substituted or unsubstituted C3-8 cycloalkyl, and substituted or unsubstituted heterocyclic group;
- R1 and R2 may be the same or different and are independently selected from hydrogen, halogen, and substituted or unsubstituted C1-6 alkyl, or both R1 and R2 directly bound to the carbon atom to which they are attached, maybe joined to form an oxo group (═O) or a substituted or unsubstituted saturated or unsaturated 3-10 member ring, which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NRa and S;
- each occurrence of X is independently selected from CR3 or N;
- and
- each occurrence of R3 is independently selected from hydrogen, hydroxy, halogen, carboxyl, cyano, nitro, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkylalkyl, substituted or unsubstituted cycloalkenylalkyl substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted heterocyclic ring, substituted heterocyclylalkyl ring, substituted or unsubstituted guanidine, —COORx, —C(O)Rx, —C(S)Rx, —C(O)NRxRy, —C(O)ONRxRy, —NRyRz, —NRxCONRyRz, —N(Rx)SORy, —N(Rx)SO2Ry, —(═N—N(Rx)Ry), —NRxC(O)ORy, —NRxRy, —NRxC(O)Ry—, —NRxC(S)Ry —NRxC(S)NRyRz, —SONRxRy—, —SO2NRxRy—, —ORx, —ORxC(O)NRyRz, —ORxC(O)ORy—, —OC(O)Rx, —OC(O)NRxRy, —RxNRyC(O)Rz, —RxORy, —RxC(O)ORy, —RxC(O)NRyRz, —RxC(O)Rx, —RxOC(O)Ry, —SRx, —SORx, —SO2Rx, and —ONO2, wherein Rx, Ry and Rz in each of the above groups can be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkylalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted heterocyclic ring, substituted or unsubstituted heterocyclylalkyl ring, or substituted or unsubstituted amino, or any two of Rx, Ry and Rz may be joined to form a substituted or unsubstituted saturated or unsaturated 3-10 membered ring, which may optionally include heteroatoms which may be the same or different and are selected from O, S, or NRx wherein Rx is hydrogen or substituted or unsubstituted alkyl;
- each occurrence of R5 is hydrogen, C1-6 alkyl or halogen;
- each occurrence of Ra may be the same or different and are independently selected from hydrogen, halogen, hydroxy, cyano, substituted or unsubstituted (C1-6)alkyl, —NRcRd (wherein Rc and Rd are independently hydrogen, halogen, hydroxy, cyano, substituted or unsubstituted (C1-6)alkyl, and (C1-6)alkoxy) and —ORc(wherein Rc is substituted or unsubstituted (C1-6)alkyl);
- n is 1, 2, 3 or 4;
- and
- p is 0, 1, 2, 3, 4 or 5.
9 more elements
A compound selected from:
- 2-[(6-Amino-9H-purin-9-yl) methyl]-6-bromo-3-phenyl-4H-chromen-4-one;
- 6-Bromo-2-(morpholinomethyl)-3-phenyl-4H-chromen-4-one;
- 6-Bromo-2-(morpholinomethyl)-3-phenyl-4H-chromen-4-one hydrochloride;
- 2-[(6-Amino-9H-purin-9-yl) methyl]-3-phenyl-4H-chromen-4-one;
- 2-(Morpholinomethyl)-3-phenyl-4H-chromen-4-one;
- 2-(Morpholinomethyl)-3-phenyl-4H-chromen-4-one hydrochloride;
- 2-[(1H-Benzo[d]imidazol-1-yl) methyl]-6-bromo-3-phenyl-4H-chromen-4-one;
- 6-Bromo-2-[(4-methyl-1H-benzo[d]imidazol-1-yl) methyl]-3-phenyl-4H-chromen-4-one;
- 2-[(1H-benzo[d]imidazol-1-yl) methyl]-3-phenyl-4H-chromen-4-one;
- 2-[(4-methyl-1H-benzo[d]imidazol-1-yl)methyl]-3-phenyl-4H-chromen-4-one;
- 2-[(6-Chloro-9H-purin-9-yl)methyl]-3-phenyl-4H-chromen-4-one;
- 6-Bromo-2-[(6-chloro-9H-purin-9-yl)methyl]-3-phenyl-4H-chromen-4-one;
- 2-[(1H-Imidazol-1-yl)methyl]-3-phenyl-4H-chromen-4-one;
- 2-((4-Amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-6-bromo-3-phenyl-4H-chromen-4-one;
- 2-[(6-Amino-9H-purin-9-yl)methyl]-6-bromo-3-(4-fluorophenyl)-4H-chromen-4-one;
- 2-[(6-Amino-9H-purin-9-yl)methyl]-3-(4-fluorophenyl)-4H-chromen-4-one;
- 6-Bromo-3-(4-fluorophenyl)-2-(morpholinomethyl)-4H-chromen-4-one;
- 6-Bromo-3-(4-fluorophenyl)-2-(morpholinomethyl)-4H-chromen-4-one hydrochloride;
- 3-(4-fluorophenyl)-2-(morpholinomethyl)-4H-chromen-4-one;
- 3-(4-fluorophenyl)-2-(morpholinomethyl)-4H-chromen-4-one hydrochloride;
- 2-[(6-Amino-9H-purin-9-yl)methyl]-6-bromo-3-o-tolyl-4H-chromen-4-one;
- 7-[(6-Bromo-4-oxo-3-phenyl-4H-chromen-2-yl)methyl]-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione;
- 2-(1-(6-Amino-9H-purin-9-yl)ethyl)-6-bromo-3-phenyl-4H-chromen-4-one;
- 2-(1-(6-Amino-9H-purin-9-yl)ethyl)-3-phenyl-4H-chromen-4-one;
- 2-(1-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-6-bromo-3-phenyl-4H-chromen-4-one;
- 2-((6-Amino-9H-purin-9-yl)methyl)-6-methoxy-3-phenyl-4H-chromen-4-one;
- 2-(1-(6-Amino-9H-purin-9-yl)ethyl)-6-bromo-3-(2-fluorophenyl)-4H-chromen-4-one;
- 2-((6-Amino-9H-purin-9-yl)methyl)-6-bromo-3-(2-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-Amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-3-phenyl-4H-chromen-4-one;
- 2-(1-(6-Amino-9H-purin-9-yl) propyl)-3-phenyl-4H-chromen-4-one;
- 2-(1-(6-Amino-9H-purin-9-yl)ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-((6-Amino-9H-purin-9-yl)methyl)-3-(2-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(6-Amino-9H-purin-9-yl)ethyl)-3-(2-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(6-Amino-9H-purin-9-yl)propyl)-3-(2-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(6-amino-9H-purin-9-yl)propyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(6-Amino-9H-purin-9-yl)propyl)-3-(4-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(6-amino-9H-purin-9-yl)propyl)-6-fluoro-3-phenyl-4H-chromen-4-one;
- 2-(1-(6-Amino-9H-purin-9-yl)ethyl)-3-(4-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(6-Amino-9H-purin-9-yl)ethyl)-6-fluoro-3-phenyl-4H-chromen-4-one;
- 2-(1-(4-Amino-3-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-3-phenyl-4H-chromen-4-one;
- 2-(1-(4-Amino-3-(3-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-3-phenyl-4H-chromen-4-one;
- 2-(1-(6-Amino-9H-purin-9-yl)ethyl)-3-o-tolyl-4H-chromen-4-one;
- 2-(1-(6-amino-9H-purin-9-yl)ethyl)-6-fluoro-3-(2-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(6-Amino-9H-purin-9-yl)ethyl)-3-(3,5-difluorophenyl)-4H-chromen-4-one;
- 2-(1-(6-amino-9H-purin-9-yl)ethyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-hydroxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-((4-Amino-3-(3-methoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-3-phenyl-4H-chromen-4-one;
- 2-((4-Amino-3-(3-hydroxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-3-phenyl-4H-chromen-4-one;
- 2-((4-amino-3-(3-methoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-((4-amino-3-(3-hydroxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-((4-Amino-3-iodo-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-3-phenyl-4H-chromen-4-one;
- 2-(1-(4-amino-3-iodo-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-phenyl-4H-chromen-4-one;
- 2-(1-(4-amino-3-iodo-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-((4-amino-3-iodo-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-6-fluoro-3-phenyl-4H-chromen-4-one;
- 2-(1-(4-amino-3-iodo-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-6-fluoro-3-phenyl-4H-chromen-4-one;
- 2-(1-(4-amino-3-iodo-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-iodo-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) propyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-((4-amino-3-(pyridin-3-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-3-phenyl-4H-chromen-4-one;
- 2-((4-amino-3-(3-hydroxyprop-1-ynyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-3-phenyl-4H-chromen-4-one;
- 2-((4-amino-3-(1H-pyrazol-4-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-3-phenyl-4H-chromen-4-one;
- 2-((4-amino-3-(3-(hydroxymethyl) phenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-3-phenyl-4H-chromen-4-one;
- 2-((4-amino-3-(1H-indazol-4-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-3-phenyl-4H-chromen-4-one;
- 2-((4-amino-3-(3-fluorophenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-3-phenyl-4H-chromen-4-one;
- 2-((4-amino-3-(3-hydroxypropyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-3-phenyl-4H-chromen-4-one;
- N-(3-(4-amino-1-((4-oxo-3-phenyl-4H-chromen-2-yl) methyl)-1H-pyrazolo [3, 4-d]pyrimidin-3-yl) phenyl) acetamide;
- 2-((4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-3-phenyl-4H-chromen-4-one;
- 2-((4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-3-phenyl-4H-chromen-4-one;
- 2-((4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-((4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(1H-pyrazol-4-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-phenyl-4H-chromen-4-one;
- 2-(1-(4-amino-3-(1H-indazol-6-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-phenyl-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-hydroxy-3-methylbut-1-ynyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-phenyl-4H-chromen-4-one;
- 2-(1-(4-amino-3-(1H-pyrazol-4-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-((4-amino-3-(1H-indazol-6-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-3-phenyl-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(1H-indazol-4-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3, 5-dimethyl-1H-pyrazol-4-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-methyl-1H-indazol-6-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(1H-indazol-6-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(2-(hydroxymethyl) phenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(4-fluoro-3-methoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(4-fluoro-3-hydroxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-hydroxyprop-1-ynyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-fluoro-4-methoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-fluoro-4-hydroxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-chloro-5-methoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-chloro-5-hydroxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-(trifluoromethoxy) phenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(4-methoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(4-hydroxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-((6-amino-9H-purin-9-yl) methyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(4-fluoro-2-methoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(4-fluoro-2-hydroxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-((4-amino-3-(3-aminophenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-3-phenyl-4H-chromen-4-one;
- 2-((4-amino-3-(3-methyl-1H-indazol-6-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-3-phenyl-4H-chromen-4-one;
- 2-(1-(4-amino-3-(2-aminopyrimidin-5-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(1H-indol-6-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(4-chloro-3-methoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(4-chloro-3-hydroxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(2-chloro-5-methoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(2-chloro-5-hydroxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3, 4-dimethoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3, 4-dihydroxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-((4-amino-3-(3-methyl-1H-indazol-6-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(1H-indol-5-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-Amino-3-(3-methyl-1H-indol-5-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- tert-butyl-(5-(4-amino-1-(1-(3-(3-fluorophenyl)-4-oxo-4H-chromen-2-yl) ethyl)-1H-pyrazolo [3, 4-d] pyrimidin-3-yl) thiophen-2-yl) methylcarbamate
- 2-(1-(4-amino-3-(5-(aminomethyl) thiophen-2-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-((4-amino-3-(3-methyl-1H-indazol-6-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-6-fluoro-3-phenyl-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-methyl-1H-indazol-6-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-phenyl-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-methyl-1H-indazol-6-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-6-fluoro-3-phenyl-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-methyl-1H-indazol-5-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- N-(4-(4-amino-1-(1-(3-(3-fluorophenyl)-4-oxo-4H-chromen-2-yl) ethyl)-1H-pyrazolo [3, 4-d] pyrimidin-3-yl) phenyl) acetamide;
- 2-(1-(4-amino-3-(4-aminophenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-methyl-1H-indazol-6-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(2, 3-dihydrobenzofuran-5-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-ethyl-1H-indazol-6-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-methyl-1H-indol-6-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(2-methoxypyrimidin-5-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 4-(4-amino-1-(1-(3-(3-fluorophenyl)-4-oxo-4H-chromen-2-yl) ethyl)-1H-pyrazolo [3, 4-d]pyrimidin-3-yl) thiophene-2-carbaldehyde;
- 2-(1-(4-amino-3-(5-(hydroxymethyl) thiophen-3-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(2-methyl-1H-benzo[d]imidazol-5-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-methyl-1H-indazol-6-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) propyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-methyl-1H-indol-6-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-((6-amino-9H-purin-9-yl) methyl)-6-fluoro-3-phenyl-4H-chromen-4-one;
- 2-((6-amino-9H-purin-9-yl) methyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-((4-amino-3-(3-fluoro-5-methoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-((4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-methoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-hydroxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-((4-amino-3-(1H-pyrazol-4-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-6-fluoro-3-phenyl-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3, 5-difluoro-4-methoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3, 5-difluoro-4-hydroxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-((4-amino-3-(3, 5-difluoro-4-methoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-((4-amino-3-(3, 5-difluoro-4-hydroxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) methyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one;
- (+)-2-(1-(4-amino-3-(3-methyl-1H-indazol-6-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- (−)-2-(1-(4-amino-3-(3-methyl-1H-indazol-6-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3, 5-dimethoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(4-methoxy-3, 5-dimethylphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(2-fluoro-5-isopropoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl) 3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(2, 3-dihydrobenzo[b] [1, 4] dioxin-6-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1—yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(1-benzyl-1H-pyrazol-4-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(2-methylpyridin-4-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3, 4-dihydro-2H-benzo[b] [1, 4] dioxepin-7-yl)-1H-pyrazolo [3, 4-d]pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(6-morpholinopyridin-3-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(dibenzo [b, d] furan-4-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(4-(benzyloxy)-3-chlorophenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-chloro-4-isopropoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-(dimethylamino) phenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(4-ethoxy-3-fluorophenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(4-isopropoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(4-(trifluoromethoxy) phenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(3-(4-acetylphenyl)-4-amino-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(4-(benzyloxy) phenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(4-(dimethylamino) phenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(4-(methylsulfonyl) phenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-ethoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(benzo[b]thiophen-2-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(5-chlorothiophen-2-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3, 5-dimethylisoxazol-4-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-propoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(furan-2-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(4-ethoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-chloro-4-methoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-fluoro-4-isopropoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(6-fluoropyridin-3-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(pyrimidin-5-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-(methoxymethyl) phenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(6-hydroxynaphthalen-2-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-isopropoxyphenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-Chloro-7H-pyrrolo [2, 3-d] pyrimidin-7-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-Chloro-1H-pyrazolo [3, 4-b] pyridin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-Chloro-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-Chloro-5H-pyrrolo [3, 2-d] pyrimidin-5-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(1, 3-dimethyl-1H-indazol-6-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(2, 3-dimethyl-2H-indazol-6-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(6-methoxynaphthalen-2-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(benzo[b]thiophen-3-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(2, 4-dimethoxypyrimidin-5-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(6-ethoxynaphthalen-2-yl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 3-(4-amino-1-(1-(3-(3-fluorophenyl)-4-oxo-4H-chromen-2-yl) ethyl)-1H-pyrazolo [3, 4-d]pyrimidin-3-yl)-N-cyclopropylbenzamide;
- 2-(1-(4-amino-3-(3-(morpholine-4-carbonyl) phenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- 2-(1-(4-amino-3-(3-(difluoromethoxy) phenyl)-1H-pyrazolo [3, 4-d] pyrimidin-1-yl) ethyl)-3-(3-fluorophenyl)-4H-chromen-4-one;
- and
- 5-(4-amino-1-(1-(3-(3-fluorophenyl)-4-oxo-4H-chromen-2-yl) ethyl)-1H-pyrazolo [3, 4-d]pyrimidin-3-yl) furan-2-carbaldehyde;
- and pharmaceutically acceptable salts thereof.
187 more elements
A compound of formula
- or a tautomer thereof, N-oxide thereof, pharmaceutically acceptable ester thereof, prodrug, or pharmaceutically acceptable salt thereof, wherein
- each occurrence of R is independently selected from hydrogen, halogen, —ORa, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C2-6 alkenyl, substituted or unsubstituted C2-6 alkynyl, substituted or unsubstituted C3-8 cycloalkyl, and substituted or unsubstituted heterocyclic group;
- R1 and R2 may be the same or different and are independently selected from hydrogen, halogen, and substituted or unsubstituted C1-6 alkyl, or both R1 and R2 directly bound to the carbon atom to which they are attached, may be joined to form a substituted or unsubstituted saturated or unsaturated 3-10 member ring, which may optionally include one or more heteroatoms which may be the same or different and are selected from O, NRa and S;
- Cy1 is a monocyclic group selected from substituted or unsubstituted cycloalkyl, substituted heterocyclic group, substituted or unsubstituted aryl and unsubstituted heteroaryl;
- Cy2 is selected from a substituted heterocyclic group, substituted aryl and substituted or unsubstituted heteroaryl;
- L1 is absent or selected from —(CRaRb)q— or —C(═Y)—;
- each occurrence of Ra and Rb may be the same or different and are independently selected from hydrogen, halogen, hydroxy, cyano, substituted or unsubstituted (C1-6)alkyl, and —ORc (wherein Rc is substituted or unsubstituted (C1-6)alkyl) or Ra and Rb may be joined to form a substituted or unsubstituted saturated or unsaturated 3-10 member ring, which may optionally include one or more heteroatoms which may be the same or different and are selected from O, S, or NRd wherein Rd is hydrogen or substituted or unsubstituted (C1-6)alkyl;
- Y is selected from O, S, and NRa;
- n is an integer from 1 to 4;
- and
- q is 0, 1 or 2.
8 more elements
Dependencies are inferred from the claim text.