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US 10,253,010 B2Granted
C-glycoside derivative
AssigneeSihuan Pharmaceutical Holdings Group Ltd.
InventorFrank Wu
Life of this patent
Estimating the term…
Abstract
The present invention involves a compound represented by general formula (I), a derivative thereof and a use thereof: wherein R1, R2, R3, R4, R5a, R5b, R5c and X are defined as in the description.
Claims14
An intermediate useful for preparing a compound of general formula (I), or a pharmaceutically acceptable salt thereof or a stereoisomer thereof,
- wherein said intermediate is a compound selected from the group consisting of a compound represented by general formula (II), a compound represented by general formula (III) and a compound represented by general formula (IV), or a pharmaceutically acceptable salt thereof or a stereoisomer thereof,
- wherein R1 and R2 each independently represent hydrogen, —OH, —OR6, alkyl, —CF3, —OCHF2, —OCF3, halogen, —CN, C2-6alkynyl, C2-6alkenyl, cycloalkyl, C2-4alkenyl-C1-4alkyl, C2-4alkynyl-C1-4alkyl, C2-4alkenyl-C1-4alkoxy, C2-4alkynyl-C1-4alkoxy, C3-7cycloalkyl-C1-4alkyl, —NR7R7a, carbonyl, —COOR6a, —COOH, —COR7b, —CH(OH)R7c, —CH(OR6g)R7d, —CONR7R7a, —NHCOR6b, —NHSO2R6c, —NHSO2aryl, aryl, —SR6d, —SOR6e, —SO2R6f, —SO2aryl, or
- R1 and R2 together with carbon atoms attached thereto form a ring or a 3-14 membered heterocyclic ring containing 1-4 heteroatoms selected from N, O, S, SO and/or SO2;
- R3 represents OR8, a 5-12 membered spiro-ring group, a 5-12 membered bridged-ring group or a 6-14 membered fused-ring group, or a 5-12 membered spiro-ring group, a 5-12 membered bridged-ring group or a 6-14 membered fused-ring group in which one or more carbon atoms are replaced with one or more heteroatoms selected from N, O, S, SO and/or SO2;
- R4, R5a, R5b and R5c respectively represent hydrogen, (C1-18-alkyl)carbonyl, (C1-18-alkyl)oxycarbonyl, arylcarbonyl, or aryl-(C1-3alkyl)carbonyl;
- R8 represents a 6 membered fused-ring group;
- R6, R6a, R6b, R6c, R6d, R6e and R6f respectively represent alkyl or cycloalkyl, or alkyl or cycloalkyl in which one or more carbon atoms are replaced with one or more heteroatoms selected from N, O, S, SO and/or SO2;
- R7, R7a, R7b, R7c and R7d respectively represent hydrogen, alkyl, aryl, alkylaryl or cycloalkyl, or R7 and R7a together with the nitrogen attached thereto form a 3-14 membered heterocyclyl containing 1-4 heteroatoms selected from N, O, S, SO and/or SO2;
- X represents a chemical bond, NH, O, S, SO, SO2 or an alkylene, said alkylene can be further substituted by one or more substituents, which comprise halogen, hydroxyl, C1-4alkyl, cycloalkyl, C1-4alkoxy, C1-4alkyl that is substituted by halogen;
- wherein the alkyl, the cycloalkyl, the aryl, the heterocyclyl, the spiro-ring group, the bridged-ring group, and the fused-ring group, as mentioned above, can be further substituted by one or more substituents, which comprise halogen, hydroxyl, amino, carboxyl, alkyl, alkoxy, aminosulfonyl, carbamoyl, C1-4alkoxy that is substituted by halogen, and C1-4alkyl that is substituted by halogen, hydroxyl, amino, and/or carboxyl.
7 more elements
process for preparing a compound represented by general formula (I), a pharmaceutically acceptable salt thereof, or a stereoisomer thereof,
- which process comprises that a compound represented by general formula (IV), a pharmaceutically acceptable salt thereof, or a stereoisomer thereof, and a compound represented by general formula (V), a pharmaceutically acceptable salt thereof, or a stereoisomer thereof are subjected to a nucleophilic reaction,
- wherein R1 and R2 each independently represent hydrogen, —OH, —OR6, alkyl, —CF3, —OCHF2, —OCF3, halogen, —CN, C2-6alkynyl, C2-6alkenyl, cycloalkyl, C2-4alkenyl-C1-4alkyl, C2-4alkynyl-C1-4alkyl, C2-4alkenyl-C1-4alkoxy, C2-4alkynyl-C1-4alkoxy, C3-7cycloalkyl-C1-4alkyl, —NR7R7a, carbonyl, —COOR6a, —COOH, —COR7b, —CH(OH)R7c, —CH(OR6g)R7d, —CONR7R7a, —NHCOR6b, —NHSO2R6c, —NHSO2aryl, aryl, —SR6d, —SOR6e, —SO2R6f, —SO2aryl, or
- R1 and R2 together with carbon atoms attached thereto form a ring or a 3-14 membered heterocyclic ring containing 1-4 heteroatoms selected from N, O, S, SO and/or SO2;
- R3 represents OR8, a 5-12 membered spiro-ring group, a 5-12 membered bridged-ring group or a 6-14 membered fused-ring group, or a 5-12 membered spiro-ring group, a 5-12 membered bridged-ring group or a 6-14 membered fused-ring group in which one or more carbon atoms are replaced with one or more heteroatoms selected from N, O, S, SO and/or SO2;
- R4, R5a, R5b and R5c respectively represent hydrogen, (C1-18-alkyl)carbonyl, (C1-18-alkyl)oxycarbonyl, arylcarbonyl, or aryl-(C1-3alkyl)carbonyl;
- R8 represents a 6 membered fused-ring group;
- R6, R6a, R6b, R6c, R6d, R6e and R6f respectively represent alkyl or cycloalkyl, or alkyl or cycloalkyl in which one or more carbon atoms are replaced with one or more heteroatoms selected from N, O, S, SO and/or SO2;
- R7, R7a, R7b, R7c and R7d respectively represent hydrogen, alkyl, aryl, alkylaryl or cycloalkyl, or R7 and R7a together with the nitrogen attached thereto form a 3-14 membered heterocyclyl containing 1-4 heteroatoms selected from N, O, S, SO and/or SO2;
- X represents a chemical bond, NH, O, S, SO, SO2 or an alkylene, said alkylene can be further substituted by one or more substituents, which comprise halogen, hydroxyl, C1-4alkyl, cycloalkyl, C1-4alkoxy, C1-4alkyl that is substituted by halogen;
- wherein the alkyl, the cycloalkyl, the aryl, the heterocyclyl, the spiro-ring group, the bridged-ring group, and the fused-ring group, as mentioned above, can be further substituted by one or more substituents, which comprise halogen, hydroxyl, amino, carboxyl, alkyl, alkoxy, aminosulfonyl, carbamoyl, C1-4alkoxy that is substituted by halogen, and C1-4alkyl that is substituted by halogen, hydroxyl, amino, and/or carboxyl.
7 more elements
Dependencies are inferred from the claim text.