848258-31-1Relevant academic research and scientific papers
A practical synthesis of the PPARα agonist, (R)-K-13675, starting from (S)-2-hydroxybutyrolactone
Yamazaki, Yukiyoshi,Araki, Takaaki,Koura, Minoru,Shibuya, Kimiyuki
, p. 8155 - 8158 (2008/12/21)
A practical synthesis of optically pure PPARα agonist, (R)-K-13675, is described. This process is based on the use of (S)-2-hydroxybutyrolactone, which can be transformed into the requisite n-butyl (S)-2-hydroxybutanoate in an efficient manner. A key reaction is the etherification between the phenol and n-butyl (S)-2-trifluoromethanesulfonyloxybutanoate to give the phenyl ether in excellent yield without loss of optical purity.
Enantioselective synthesis of the PPARα agonist (R)-K-13675 via (S)-2-hydroxybutyrolactone
Yamazaki, Yukiyoshi,Araki, Takaaki,Koura, Minoru,Shibuya, Kimiyuki
, p. 1017 - 1022 (2008/12/22)
Enantioselective synthesis of enantiomerically pure PPARα agonist (R)-K-13675 can be achieved starting from (S)-2-hydroxybutyrolactone. An important intermediate, 2-(aryloxy)butyrolactone, was prepared by reaction of the phenol with (S)-2-hydroxybutyrolactone in excellent yield without loss of enantiomeric purity using the Mitsunobu reaction, followed by conversion into the 2-(aryloxy)butanoic acid via the 2-(aryloxy)-4-iodobutanoate by cleavage of the lactone on exposure to iodotrimethylsilane, followed by hydrogenolysis and hydrolysis. Georg Thieme Verlag Stuttgart.
PROCESSES FOR PRODUCTION OF OPTICALLY ACTIVE PPAR-ACTIVATING COMPOUNDS AND INTERMEDIATES FOR PRODUCTION THEREOF
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Page/Page column 11, (2008/06/13)
The invention provides a process for producing an optically active butyric acid compound and a production intermediate therefor at high yield and high purity. The present invention provides a process for producing Compound (6), including reacting Compound (1) with optically active 2-trifluoromethanesulfonyloxybutyrolactone (2a) in the presence of a base or reacting optically active 2-hydroxybutyrolactone (2b) under Mitsunobu reaction conditions, to thereby form Compound (3); reacting Compound (3) with an alcohol and a halogenating agent, to thereby form Compound (4) ; dehalogenating Compound (4), to thereby form Compound (5); and de-esterifying Compound (5).
Design and synthesis of highly potent and selective human peroxisome proliferator-activated receptor α agonists
Yamazaki, Yukiyoshi,Abe, Kazutoyo,Toma, Tsutomu,Nishikawa, Masahiro,Ozawa, Hidefumi,Okuda, Ayumu,Araki, Takaaki,Oda, Soichi,Inoue, Keisuke,Shibuya, Kimiyuki,Staels, Bart,Fruchart, Jean-Charles
, p. 4689 - 4693 (2008/02/11)
A combination of benzoxazole, phenoxyalkyl side chain, and phenoxybutyric acids was identified as a highly potent and selective human peroxisome proliferator-activated receptor α (PPARα) agonist. The synthesis, structure-activity relationship (SAR) studies, and in vivo activities of the representative compounds are described.
PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE PPAR-ACTIVATING COMPOUND AND INTERMEDIATE OF THE SAME
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, (2008/06/13)
A process for obtaining a compound (1) and an intermediate thereof in high yield and high optical yield is provided. A process for producing a compound (4), the process including reacting a compound (2) with a compound (3) in the presence of a base; and a process for producing a compound (1), the process including reacting a compound (2) with a compound (3) in the presence of a base to yield a compound (4) and then deesterifying the compound (4). wherein R represents an alkyl group having 1 to 6 carbon atoms or an aralkyl group having 7 to 8 carbon atoms.
OPTICALLY ACTIVE PPAR-ACTIVATING COMPOUND INTERMEDIATE AND METHOD FOR PRODUCING SAME
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Page/Page column 10-11, (2008/06/13)
The present invention provides a production intermediate for compound (A-1) and a method for producing the intermediate at high yield and high optical yield. The present invention provides a method for producing compound (3) characterized in that compound
PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE PPAR-ACTIVATING COMPOUND AND INTERMEDIATE OF THE SAME
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Page/Page column 11-13; 15-16, (2008/06/13)
A process for producing a compound (4) comprising the step of reacting a compound (2) with a compound (3) in the presence of a base; and a process for producing a compound (1) comprising the step of reacting a compound (2) with a compound (3) in the prese
PPAR-activating compound and pharmaceutical composition comprising the compound
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Page/Page column 16, (2008/06/13)
A compound represented by the following formula (1): Or a salt thereof; and therapeutic durgs containing the compound. The compound selectively activates PPARα.
