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Details for Patent: 6,307,052

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Details for Patent: 6,307,052

Title: Acid-addition salts of optically active piperidine compound and process for producing the same
Abstract:The present invention is to provide a benzenesulfonic acid salt and a benzoic acid salt of (S)-4-[4-[(4-chlorophenyl) (2-pyridyl)methoxy]piperidino]butanoic acid represented by the formula (I): ##STR1## wherein * represents an asymmetric carbon, which are excellent in antihistaminic activity and anti-allergic activity, and a process for producing the same.
Inventor(s): Kita; Jun-ichiro (Ube, JP), Fujiwara; Hiroshi (Ube, JP), Takamura; Shinji (Ube, JP), Yoshioka; Ryuzo (Osaka, JP), Ozaki; Yasuhiko (Osaka, JP), Yamada; Shin-ichi (Takarazuka, JP)
Assignee: Ube Industries, Ltd. (Yamaguchi, JP) Tanabe Seiyaku Co., Ltd. (Osaka, JP)
Filing Date:Jun 25, 1999
Application Number:09/331,792
Claims:1. A process for preparing a benzenesulfonic acid salt or a benzoic acid salt of the optically active piperidine compound represented by formula (I) ##STR13##

which comprises reacting (.+-.)-4-[(4-chlorophenyl)(2-pyridyl)methoxy]-piperidine with an optically active propionic acid compound represented by the formula (VII): ##STR14##

wherein Y represents a hydrogen atom or a halogen atom; Z represents a lower alkoxy group; and * represents an asymmetric carbon, or an optically active N-acyl-amino acid; separating and collecting a less soluble diastereomeric salt by utilizing the difference in solubilities of the formed two kinds of diastereomeric salts; decomposing the resulting salt; reacting the resulting (S)-4-[4-chlorophenyl)(2- pyridyl)methoxy]piperidine with an ester represented by the formula (V): ##STR15##

wherein R represents a lower alkyl group, and W represents a leaving group such as a halogen atom and a reactive ester group,

to obtain (S)-4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidino] butanoic acid ester represented by the formula (VI): ##STR16##

wherein R and * have the same meaning as defined above; hydrolyzing the resulting compound; and reacting the hydrolyzed compound with benzenesulfonic acid or benzoic acid to form a salt.

2. A process for preparing an optically active piperidine intermediate represented by the formula (IV): ##STR17##

wherein * represents an asymmetric carbon, which comprises reacting a racemic piperidine compound represented by the formula (III): ##STR18##

with an optically active propionic acid compound represented by the formula (VII): ##STR19##

wherein Y represents a hydrogen atom or a halogen atom;

Z represents a lower alkoxy group; and * has the same meanings as defined above,

or an optically active N-acyl-amino acid; separating and collecting one of the diastereomeric salts by utilizing the difference in solubilities of the formed two kinds of diastereomeric salts; and decomposing the resulting salt.
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