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US 2013/0296599 A1Published application
Phenylglyoxylic acid derivatives and their preparation and use
AssigneeTransTech Pharma, Inc.
InventorsDharma Rao Polisetti, Kalpathy Santhosh, Muralidhar Bondlela, Robert Carl Andrews, Thomas Scott Yokum, Eugene Campian, Rajashaker Kache
Life of this patent
Estimating the term…
Abstract
The invention provides novel phenylglyoxylic acid derivatives, which may be useful as intermediates for preparing stereoisomerically enriched drug compounds. The invention also provides methods of making phenylglyoxylic acid derivatives, and uses of phenylglyoxylic acid derivatives.
Claims21
A compound of Formula (I)
- wherein:
- R1 and R5 are hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, or C1-4 haloalkoxy;
- R3 is halogen, hydroxyl, cyano, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, or C1-4 haloalkoxy;
- one of R2 and R4 is halogen, hydroxyl, cyano, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, or C1-4 haloalkoxy, while the other is hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, or C1-4 haloalkoxy;
- R6, R7, R8, R9 are hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, or C1-4 haloalkoxy;
- R10 is hydrogen, C1-6 alkyl, or an alkali metal cation;
- and
- Z is C1-6 alkylene, which is optionally substituted one or more times by substitutents selected independently from the group consisting of halo, cyano, C1-4 haloalkyl, C1-4 haloalkoxy, phenyl, and oxo.
5 more elements
A method of making a phenylglyoxylic acid derivative comprising oxidizing a compound of Formula (II)
- wherein:
- R1 and R5 are hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, or C1-4 haloalkoxy;
- R3 is halogen, hydroxyl, cyano, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, or C1-4 haloalkoxy;
- one of R2 and R4 is halogen, hydroxyl, cyano, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, or C1-4 haloalkoxy, while the other is hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, or C1-4 haloalkoxy;
- R6, R7, R8, R9 are hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, or C1-4 haloalkoxy;
- R10 is hydrogen, C1-6 alkyl, or an alkali metal cation;
- and
- Z is C1-6 alkylene, which is optionally substituted one or more times by substitutents selected independently from the group consisting of halo, cyano, C1-4 haloalkyl, C1-4 haloalkoxy, phenyl, and oxo.
5 more elements
A method of reducing a phenylglyoxylic acid derivative comprising reducing a compound of Formula (I)
- wherein:
- R1 and R5 are hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, or C1-4 haloalkoxy;
- R3 is halogen, hydroxyl, cyano, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, or C1-4 haloalkoxy;
- one of R2 and R4 is halogen, hydroxyl, cyano, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, or C1-4 haloalkoxy, while the other is hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, or C1-4 haloalkoxy;
- R6, R7, R8, R9 are hydrogen, halogen, C1-4 alkyl, C1-4 alkoxy, C1-4 haloalkyl, or C1-4 haloalkoxy;
- R10 is hydrogen, C1-6 alkyl, or an alkali metal cation;
- and
- Z is C1-6 alkylene, which is optionally substituted one or more times by substitutents selected independently from the group consisting of halo, cyano, C1-4 haloalkyl, C1-4 haloalkoxy, phenyl, and oxo.
5 more elements
Dependencies are inferred from the claim text.