Kissei Pharmaceutical Co., Ltd.

Tetsuji Ozawa

Ken Kikuchi

Minoru Kubota

Kiyoshi Kasai

Masahiro Kobayashi

Nobuhiko Fushimi

Hideki Takeuchi

Takehiro Ishikawa

Hidetoshi Isawa

Toshiaki Yamaguchi

Ritsu Suzuki

Masaaki Ban

Koji Kamata

Junichi Sonehara

Takashi Yanagi

The present invention relates to a method for preparing the glucopyranosyloxypyrazole derivatives which are useful as agents for the prevention or treatment of a disease associated with hyperglycemia such as diabetes, diabetic complications, obesity or the like. A glucopyranosyloxypyrazole derivative can be easily and efficiently prepared by allowing a benzylpyrazole derivative represented by the general formula: wherein R, R, R, Rand Rmay be the same or different, for example each of them is a hydrogen atom, a halogen atom or an alkyl, alkoxy, arylmethyloxy group or the like, Ris an alkyl group, for example Ris a hydrogen atom or an alkyl, alkoxy, arylmethyloxy group or the like, to react with a compound represented by the general formula: wherein as an example, PGis a pivaloyl group or the like, as an example, Xis a bromine atom or the like, therefore the present invention is extremely useful as a method for preparing pharmaceutical compounds.

Process for production of glucopyranosyloxypyrazole derivative

Crystals of a salt of 4'-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethylamino]ethoxy}-3-isopropyl-3&#x2032;,5&#x2032;-dimethylbiphenyl-4-carboxylic acid. The &#x3b1; type, &#x3b2; type and &#x3b3; type crystals produced by treating hydrochloride of 4&#x2032;-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethylamino]ethoxy}-3-isopropyl-3&#x2032;,5&#x2032;-dimethylbiphenyl-4-carboxylic acid with specified solvents, which can be discriminated by the characteristic diffraction peaks of powder X-ray diffractometry and the like.

Polymorphic crystal of 4'-{2-[ (1S, 2R)&#x2014;2-  hydroxy-2- (4-hydroxyphenyl)-1-methylethylamino]ethoxy} - 3 - isopropyl-3&#x2032;, 5&#x2032; -dimethylbiphenyl- 4 - carboxylic acid hydrochloride

The present invention provides novel phenol derivatives represented by the formula: wherein the carbon atom marked with (S) represents a carbon atom in S configuration; Z represents the group represented by the formula: or the formula: wherein the carbon atoms marked with (R) represents a carbon atom in R configuration, and a method to produce a phenol derivative represented by the formula (A): (wherein the carbon atom marked with (R) and (S) have the same meanings as defined above) which comprises using any of those derivatives as an intermediate therefore.

Phenol derivatives and method of use thereof

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Joetsu, Japan

Tetsuji Ozawa