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Generated: September 23, 2017

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Title:Process for preparing benzazepine compounds or salts thereof
Abstract: This invention provides a process for preparing benzazepine compounds of the formula (1): ##STR00001## wherein X.sup.1 is a halogen atom, R.sup.1 and R.sup.2 are a lower alkyl group, or salts thereof as well as intermediate benzoic acid compounds in high yield and high purity on industrial scale, which are useful as an intermediate for preparing a pharmaceutically active 2,3,4,5-tetrahydro-1H-1-benzazepine compound having vasopressin antagonistic activity.
Inventor(s): Torisawa; Yasuhiro (Tokushima, JP), Abe; Kaoru (Tokushima, JP), Muguruma; Yasuaki (Tokushima, JP), Fujita; Shigekazu (Okazaki, JP), Ogawa; Hidenori (Tokushima, JP), Utsumi; Naoto (Tokushima, JP), Miyake; Masahiro (Tokushima, JP)
Assignee: Otsuka Pharmaceutical Co., Ltd. (Tokyo, JP)
Application Number:13/474,521
Patent Claims: 1. A highly pure 7-chloro-5-hydroxy-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-t- etrahydro-1H-1-benzazepine having a purity of more than 99.5%, or a salt thereof, which is produced by the process which comprises reducing a benzazepine compound of the formula (1): ##STR00028## wherein X.sup.1 is a halogen atom, R.sup.1 and R.sup.2 are independently a lower alkyl group, or a salt thereof in the presence of a hydrogenating agent selected from the group consisting of lithium aluminum hydride, sodium borohydride, zinc borohydride, and diborane in an amount of 0.25 to 1 mole per 1 mole of the compound (1).

2. 7-Chloro-5-hydroxy-1-[2-methyl-4-(2-methyl-benzoylamino)benzoyl]-2,3,4- ,5-tetrahydro-1H-1-benzazepine or a salt thereof, which is substantially free from at least one of the benzazepine compounds selected from 7-chloro-5-hydroxy-1-{2-methyl-4-[N-(2-methylbenzoyl)-N-(2-methyl-4-(2-me- thylbenzoylamino)benzoylamino]-benzoyl}-2,3,4,5-tetrahydro-1H-1-benzazepin- e (Compound A), 7-chloro-5-hydroxy-1-{2-methyl-4-[2-methyl-4-(2-methylbenzoylamino)benzoy- l-amino]benzoyl}-2,3,4,5-tetrahydro-1H-1-benzazepine (Compound B), 7-chloro-5-[2-methyl-4-(2-methylbenzoylamino)benzoyloxy]-1-[2-methyl-4-(2- -methylbenzoylamino)benzoyl]-2,3-dihydro-1H-1-benzazepine (Compound C), and 7-chloro-5-[2-methyl-4-(2-methylbenzoylamino)-benzoyloxy]-1-[2-methyl- -4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetra hydro-1H-1-benzazepine (Compound D), which is produced by the process which comprises reducing a benzazepine compound of the formula (1): ##STR00029## wherein X.sup.1 is a halogen atom, R.sup.1 and R.sup.2 are independently a lower alkyl group, or a salt thereof in the presence of a hydrogenating agent selected from the group consisting of lithium aluminum hydride, sodium borohydride, zinc borohydride, and diborane in an amount of 0.25 to 1 mole per 1 mole of the compound (1).

3. 7-Chloro-5-hydroxy-1-[2-methyl-4-(2-methyl-benzoylamino)benzoyl]-2,3,4- ,5-tetrahydro-1H-1-benzazepine or a salt thereof as set forth in claim 1 or 2, which is produced by the process which comprises reducing a benzazepine compound of the formula (1): ##STR00030## wherein X.sup.1 is a halogen atom, R.sup.1 and R.sup.2 are independently a lower alkyl group, or a salt thereof, in the presence of a hydrogenating agent selected from the group consisting of lithium aluminum hydride, sodium borohydride, zinc borohydride, and diborane in an amount of 0.25 to 1 mole per 1 mole of the compound (1).

4. 7-Chloro-5-hydroxy-1-[2-methyl-4-(2-methyl-benzoylamino)benzoyl]-2,3,4- ,5-tetrahydro-1H-1-benzazepine or a salt thereof as set forth in claim 1 or 2, which is produced by the process which comprises reducing a benzazepine compound of the formula (1): ##STR00031## wherein X.sup.1 is a halogen atom, R.sup.1 and R.sup.2 are independently a lower alkyl group, or a salt thereof, in the presence of a sodium borohydride hydrogenating agent in an amount of 0.25 to 1 mole per 1 mole of the compound (1).

5. 7-Chloro-5-hydroxy-1-[2-methyl-4-(2-methyl-benzoylamino)benzoyl]-2,3,4- ,5-tetrahydro-1H-1-benzazepine or a salt thereof as set forth in claim 1 or 2, which is produced by the process which comprises reducing a benzazepine compound of the formula (1): ##STR00032## wherein X.sup.1 is a halogen atom, R.sup.1 and R.sup.2 are independently a lower alkyl group, or a salt thereof, in the presence of a sodium borohydride hydrogenating agent in an amount of 0.25 to 0.5 mole per 1 mole of the compound (1).
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