- Efficient preparation of both enantiomers of 3,3,3-trifluoro-2-hydroxy-2- methylpropanoic acid catalyzed by Shinella sp. R-6 and Arthrobacter sp. S-2
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Several microorganisms that can enantioselectively hydrolyze 3,3,3-trifluoro-2-hydroxy-2-methylpropanamide have been isolated from soil samples. These strains were capable of growing in a medium containing 3,3,3-trifluoro-2-hydroxy-2-methylpropanamide as the sole nitrogen source. Among them, Shinella sp. R-6 was identified as a strain capable of exhibiting R-selective hydrolysis activity, while Arthrobacter sp. S-2 was capable of exhibiting S-selective hydrolysis activity. The preparation of both enantiomers of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid via the two-step whole-cell reaction was investigated using these two strains.
- Fuhshuku, Ken-Ichi,Watanabe, Shunsuke,Nishii, Tetsuro,Ishii, Akihiro,Asano, Yasuhisa
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p. 115 - 119
(2014/03/21)
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- Optically active fluorine-containing compounds and processes for their production
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An optically active fluorine-containing compound represented by the following formula (1) or (2) wherein A is an oxygen atom, a sulfur atom or an NH group, and R1 selected from a variety of organic group, is used in the preparation of (S)- or (R)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid.
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- Substituted N-phenyl 2-hydroxy-2-methyl-3,3,3-trifluoropropanamide derivatives which elevate pyruvate dehydrogenase activity
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A compound of formula (I) wherein: n is 1 or 2; R 1 is chloro, fluoro, bromo, methyl or methoxy; R 2 is as defined within; R 3 is as defined within; and R 4 is hydrogen or fluoro; or a pharmaceutically acceptable salt or an in vivo hydrolysable ester thereof is described. The use of compounds of formula (I) in the production of an elevation of PDH activity in a warm-blooded animal such as a human being are also described. Pharmaceutical compositions, methods and processes for preparation of compounds of formula (I) are detailed. STR1
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Page column 51
(2010/02/05)
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- Benzenesulfonamide-derivatives and their use as medicaments
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Compounds of formula (I), pharmaceutically acceptable salts or in vivo hydrolysable esters thereof, wherein: Ring X is phenyl or a six membered heteroaryl ring containing one or two ring nitrogens where said nitrogens are optionally oxidised to form the N
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Page column 73
(2010/11/30)
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- Process for producing optically active 3,3,3-Trifluoro-2-Hydroxy-2-Methylpropionic acid, and salt thereof
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There are disclosed are a diastereomer salt of formula (1): a process for producing the same, a process for producing optically active 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid of formula (2′): a novel optically active amine compound of formula (4): a novel optically active amine compound of formula (8): an imine compound of formula (7) or (11):
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- Use of compounds for the elevation of pyruvate dehydrogenase activity
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The use of compounds of the formula (I), and salts thereof; and pharmaceutically acceptable in vivo cleavable prodrugs of said compound of formula (I); and pharmaceutically acceptable salts of said compound or said prodrugs: wherein: Ring C is phenyl or a carbon linked heteroaryl ring substituted as defmed within; R1is an ortho substituent as defined within; n is 1 or 2; A—B is a linking group as defined within; R2and R3are as defined within; R4is hydroxy, hydrogen, halo, amino or methyl; in the manufacture of a medicament for use in the elevation of PDH activity in warm-blooded animals such as humans is described. Pharmaceutical compositions, methods and processes for preparation of compounds of formula (I) are also described.
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- Selection, purification, characterisation, and cloning of a novel heat-stable stereo-specific amidase from Klebsiella oxytoca, and its application in the synthesis of enantiomerically pure (R)- and (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acids and (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide
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We isolated, characterised, and cloned an enantio-specific amidase from Klebsiella oxytoca and used it to resolve (R,S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide, giving (R)3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid and (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide. The (S)-amide could then be hydrolysed chemically to (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid. The process can therefore be adapted to produce both (R)-and (S)-enantiomers of 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid, or (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide. The biocatalytic step is part of a combined chemical and biocatalytic route that starts from ethyl trifluoroacetoacetate. The products typically have a purity of greater than 98% and ee values of essentially 100% after isolation. The process has been used to produce 100-g amounts of the (S)-acid, and successfully scaled up to produce 100-kg amounts of the (R)-acid, with the biotransformation carried out at the 1500-L scale.
- Shaw, Nicholas M.,Brieden, Walter,De Riedmatten, Patricia,Roduit, Jean-Paul,Zimmermann, Bertin,Neumueller, Roman,Naughton, Andrew,Robins, Karen,Tinschert, Andreas,Schmid, Evelyne,Hischier, Marie-Louise,Venetz, Veronika,Werlen, Josef,Zimmermann, Thomas
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p. 497 - 504
(2013/09/06)
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- Tricyclic compounds
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The present invention provides tricyclic compounds which are useful for the treatment of pollakiuria and urinary incontinence and which are represented by general formula (I): (whereinR1 represents hydrogen, substituted or unsubstituted lower a
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- The synthesis of (R)- and (S)-α-trifluoromethyl-α-hydroxycarboxylic acids via enzymatic resolutions
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Kinetic resolution of 1, 1, 1-trifluoro-2-alkanone cyanohydrin acyl derivatives with Candida rugosa lipase afforded the remaining (R)-enantiomer in high selectivity (E from 30 to >200). Candida rugosa lipases from several suppliers were compared and found
- Konigsberger, Kurt,Prasad, Kapa,Repic, Oljan
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p. 679 - 687
(2007/10/03)
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- Tricyclic compounds
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The present invention relates to tricyclic compounds represented by general formula (I) which are useful as therapeutic agents for urinary incontinence: STR1 wherein R1 represents hydrogen and the like; --X1 --X2 --X3
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