Back to results
US 10,125,074 B2Granted
5-substituted-5-hydroxy-5-aryl-3-oxo-pentanoate derivatives and their enantiopure forms
AssigneeOkinawa Institute of Science and Technology School Corporation
InventorsFujie Tanaka, Dongxin Zhang
Life of this patent
Estimating the term…
Abstract
The present invention relates to novel tertiary alcohol derivatives substituted with aryl and trifluoromethyl, and optical isomers thereof. In addition, the present invention also relates to methods for the preparation and use as enantiomer recognition agent thereof. The present invention provides pharmaceutical composition and use as therapeutically active substance thereof.
Claims11
A compound of formula I:
- wherein
- A is
- B is aryl which is substituted with one or more groups selected from the group consisting of C1-7-alkyl, halogen, halogen-C1-7-alkyl, C1-7-alkoxy, halogen-C1-7-alkoxy, hydroxy, cyano, and nitro, or is heteroaryl, which is unsubstitued or substituted with one or more groups selected from the group consisting of C1-7-alkyl, halogen, halogen-C1-7-alkyl, C1-7-alkoxy, halogen-C1-7-alkoxy, hydroxy, cyano, and nitro;
- R1 and R1′ may be the same or different and each is independently selected from the group consisting of C1-7-alkyl, halogen-C1-7-alkyl, and C1-7-alkyl substituted with one or more C1-7-alkoxy;
- or
- R1 and R1′ may together form C1-7-alkylene;
- R2 is selected from the group consisting of C1-7-alkyl, halogen-C1-7-alkyl, C1-7-alkoxy, C3-7-cycloalkyloxy, halogen-C1-7-alkoxy, C1-7-alkoxy substituted with one or more C1-7-alkyl, and hydroxy;
- R3 is selected from the group consisting of hydrogen, halogen, C1-7-alkyl, halogen-C1-7-alkyl, hydroxy-C1-7-alkyl, C1-7-alkoxy, and halogen-C1-7-alkoxy;
- and
- n is 1, 2, 3, or 4;
- or a salt thereof.
8 more elements
A process for the manufacture of a compound of formula I-2a:
- wherein
- B is aryl which is substituted with one or more groups selected from the group consisting of C1-7-alkyl, halogen, halogen-C1-7-alkyl, C1-7-alkoxy, halogen-C1-7-alkoxy, hydroxy, cyano, and nitro, or is heteroaryl, which is unsubstitued or substituted with one or more groups selected from the group consisting of C1-7-alkyl, halogen, halogen-C1-7-alkyl, C1-7-alkoxy, halogen-C1-7-alkoxy, hydroxy, cyano, and nitro;
- R2 is selected from the group consisting of C1-7-alkyl, halogen-C1-7-alkyl, C1-7-alkoxy, C3-7-cycloalkyloxy, halogen-C1-7-alkoxy, C1-7-alkoxy substituted with one or more C1-7-alkyl, and hydroxy;
- R3 is selected from the group consisting of hydrogen, halogen, C1-7-alkyl, halogen-C1-7-alkyl, hydroxy-C1-7-alkyl, C1-7-alkoxy, and halogen-C1-7-alkoxy, or
- a compound of formula I-2b:
- wherein R2, R3, and B are as defined above, said process comprising
- d) reacting compound of formula 1-2:
- wherein R2, R3, and B are as defined above, with a chiral amine:
- wherein R4 and R5 are independently selected from the group of C1-7alkyl and phenyl optionally substituted with halogen, to obtain a compound of formula I-2′-1:
- wherein R2, R3, R4, R5, and B are as defined above, or
- a compound of formula I-2′-2:
- wherein R2, R3, R4, R5, and B are as defined above.
9 more elements
Dependencies are inferred from the claim text.