Kowa Company Limited

Taichi Kusakabe

Kimiyuki Shibuya

Tadaaki Ohgiya

Koichi Yamazaki

Kennosuke Matsuda

Takeshi Murakami

Katsutoshi Miyosawa

It is an object of the present invention to provide a novel form of (S)-trans-{4-[({2-[({1-[3,5-bis(trifluoromethyl)phenyl]ethyl}{5-[2-(methylsulfonyl)ethoxy]pyrimidin-2-yl}amino)methyl]-4-(trifluoromethyl)phenyl}(ethyl)amino)methyl]cyclohexyl}acetic acid, which is useful for preventing and/or treating diseases such as dyslipidemia. (S)-trans-{4-[({2-[({1-[3,5-bis(Trifluoromethyl)phenyl]ethyl}{5-[2-(methylsulfonyl)ethoxy]pyrimidin-2-yl}amino)methyl]-4-(trifluoromethyl)phenyl}(ethyl)amino)methyl]cyclohexyl}acetic acid hydrochloride.

Form of pyrimidine compound having dibenzylamine structure

A method for preparing optically active 1-bromo-1-[3,5-bis(trifluoromethyl)-phenyl]ethane having a high optical purity, which comprises the step of brominating optically active 1-[3,5-bis(trifluoromethyl)phenyl]ethanol by using, as a brominating agent, (a) a combination of a phosphorus halide and hydrogen bromide, (b) a combination of 1,2-dibromo-1,1,2,2-tetrachloroethane and an organic phosphorous compound represented by the general formula (I): P(R)(R)(R) (in the formula, R, R, and Rindependently represent a Caryl group, a Caryloxy group, a Calkyl group, a Calkoxyl group, a Ccycloalkyl group, or a Ccycloalkoxy group), or (c) a combination of N-bromosuccinimide and a dialkyl sulfide.

Method for preparing optically active 1-bromo-1[3,5-bis(trifluoromethyl)phenyl]ethane

Substantially optically pure (S)-trans-{4-[({2-[({1-[3,5-bis(trifluoromethyl)phenyl]ethyl}{5-[2-(methylsulfonyl)ethoxy]pyrimidin-2-yl}amino)methyl]-4-(trifluoromethyl)phenyl}(ethyl)amino)methyl]cyclohexyl}acetic acid, or a salt thereof, or a solvate thereof, which has actions of reducing amount of PCSK9 protein and increasing amount of LDL receptor.

Optically active dibenzylamine derivative, and method for preparing thereof

A method for preparing a trans-{4-[(alkylamino)methyl]cyclohexyl}acetic acid, which is useful as a raw material compound for manufacture of medicaments and the like, comprising the step of reducing amide group of a compound represented by the following general formula (6) (Rrepresents hydrogen atom or a Calkyl group, and Rrepresents a Calkyl group, a Ccycloalkyl group, a (Ccycloalkyl)(Calkyl) group, a Caryl group, or a Caralkyl group). 

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Chiba, Japan

Taichi Kusakabe