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US 2015/0307532 A1Published application
Thienopyrimidine inhibitors of farnesyl and/or geranylgeranyl pyrophosphate synthase
AssigneeThe Royal Institution for the Advancement of Learning/Mcgill University
InventorsYoula S. TSANTRIZOS, Judes POIRIER, Michael SEBAG, Albert BERGHUIS, Jaeok PARK, Joris WIM DE SCHUTTER
Life of this patent
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Abstract
The present invention relates to novel compounds, compositions containing same and methods for inhibiting human farnesyl pyrophosphate synthase or for the treatment or prevention of disease conditions using said compounds;
Claims17
A compound of formula I:
- or a pharmaceutically acceptable salt or solvate thereof, wherein
- X═O, NR4, or CR4R4;
- R2 is selected from H, C1-6alkyl, C3-6 cycloalkyl, C6-10aryl, 3-10 membered heterocycle, —CONHR7, —SO2NHR7;
- R3 is selected from CH[PO(OH)2]2;
- CH2PO(OH)2;
- CHR7PO(OH)2;
- CH(CO2H)2;
- CH(SO2NHR7)PO(OH)2;
- CR8R9-SO2NR7(PO(OH)2), COCO2H;
- CR8(PO(OH)2)2, CR8R9CO2H;
- CR8R9PO(OH)2, CR8R9COR10 or C1-6alkyl;
- R4 are each independently H, C1-6alkyl, aryl or 3-10 membered heterocycle;
- R5 and R6 are independently selected from H, C1-6alkyl, optionally substituted C3-6 cycloalkyl, optionally substituted C6-10aryl, optionally substituted 3-10 membered heterocycle, CH2OH, CO2H, CH2CO2H, (CH2)nPO(OH)2, (CH2)n-SO2NR7(PO(OH)2), (CH2)nSO2NR7R8, NR7R8, NH(CH2), PO(OH)2, NO2 or OR7;
- where n is an integer number from 1-3;
- R5 and R6 can also be independently selected from amino acids, natural or unnatural attached to thienopyrimidine core via a C-1-4 alkyl linker;
- R7, R8 and R9 are each independently —H, —C1-6 alkyl, —C3-6 cycloalkyl, —C6-10 aryl, 3-10 membered heterocycle or —C1-6alkyl-C6-10aryl;
- R8 and R9 can also be taken together to form a 3 to 6 membered cycoalkyl;
- and
- R10 is C1-6 alkyl, —C3-6 cycloalkyl, —C6-10 aryl or 3-10 membered heterocycle.
16 more elements
(canceled)
15-21. (canceled)
Dependencies are inferred from the claim text.