Fuji Yakuhin Co., Ltd

Yoshiyuki Iwabuchi

Junichiro Uda

Takahiro Sato

Osamu Nagata

Sachiho Miyata

Hiroshi Nakamura

Hideo Kato

Tadashi Inoue

Hiroyuki Nakano

Takamitsu Kandou

Tutomu Inoue

Nobuhide Kawasaki

Ippei Tanaka

Naoki Kurita

Tomohiko Ishikawa

To provide an industrially useful method for producing pharmaceutically useful 4-[5-(pyridin-4-yl)-1H-1,2,4-triazol-3-yl]pyridine-2-carbonitrile, and an intermediate for producing the compound. The method for producing compound represented by formula (1) is represented by the following reaction scheme, and the intermediate is represented by the following formula (4). 

Method for producing 4-[5-(pyridin-4-yl)-1H-1,2,4-triazol-3-yl]pyridine-2-carbonitrile, and intermediate thereof

To provide crystal polymorphs of 4-[5-(pyridin-4-yl)-1H-1,2,4-triazol-3-yl]pyridine-2-carbonitrile, which is a useful pharmaceutical, and a production method therefor. Through purification of a corresponding salt, recrystallization, or storage under humidified conditions, three different crystal forms; i.e., crystalline polymorphs of 4-[5-(pyridin-4-yl)-1H-1,2,4-triazol-3-yl]pyridine-2-carbonitrile are produced.

4-[5-(pyridin-4-yl)-1H-1,2,4-triazol-3-yl]pyridine-2-carbonitrile crystalline polymorph and production method therefor

A compound represented by the formula (1) or a salt thereof (represents a single bond, or a double bond; Rrepresents hydrogen atom, or an alkyl group; Rand Rrepresent hydrogen atom, or an alkyl group; Rand Rrepresent hydrogen atom, hydroxy group, an alkoxyl group, a halogen atom, or a mono- or di-alkyl-substituted amino group; Rrepresents hydrogen atom, cyano group, an alkoxycarbonyl group, or carboxy group; Rrepresents one or two of substituents on the benzene ring (the substituents are selected from hydrogen atom, a halogen atom, nitro group, cyano group, hydroxy group, amino group, an alkyl group, and an alkoxyl group); A represents a 5-membered or 6-membered non-aromatic heterocyclic ring containing one or two contiguous sulfur atoms (the sulfur atoms may independently form oxide); Wrepresents oxo group, hydrogen atom, an alkyl group, hydroxy group, an alkoxyl group, or a halogen atom; and X represents oxygen atom, or sulfur atom), or a salt thereof, which has a superior suppressing action against prostaglandin Eproduction and is useful as an active ingredient of medicaments with reduced adverse reactions such as gastrointestinal disorders. 

Phenylacetic acid derivative

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Saitama, Japan

Yoshiyuki Iwabuchi