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Claims for Patent: 7,888,362

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Claims for Patent: 7,888,362

Title:Piperazine-substituted benzothiophenes for treatment of mental disorders
Abstract: The present invention provides a heterocyclic compound represented by the general formula (1): The compound of the present invention has a wide treatment spectrum for mental disorders including central nervous system disorders, no side effects and high safety. ##STR00001##
Inventor(s): Yamashita; Hiroshi (Tokushima, JP), Ito; Nobuaki (Tokushima, JP), Miyamura; Shin (Tokushima, JP), Oshima; Kunio (Tokushima, JP), Matsubara; Jun (Tokushima, JP), Kuroda; Hideaki (Tokushima, JP), Takahashi; Haruka (Tokushima, JP), Shimizu; Satoshi (Tokushima, JP), Tanaka; Tatsuyoshi (Tokushima, JP)
Assignee: Otsuka Pharmaceutical Co., Ltd. (Tokyo, JP)
Application Number:11/659,005
Patent Claims: 1. A heterocyclic compound represented by the formula (1): ##STR00176## [wherein ring Q represented by ##STR00177## represents --NH--CH.sub.2--, --N.dbd.CH--, --CH.sub.2--NH-- or --CH.dbd.N--; and the carbon-carbon bond between the 3-position and 4-position of the heterocyclic skeleton containing Z and Y represents a single bond or a double bond); the ring Q may have at least one substituent selected from the group consisting of a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a hydroxy group, a lower alkoxy group, a halogenated lower alkyl group, an aryl group, an aryl lower alkyl group, an aryl lower alkoxy group, an arylcarbonyl group, a lower alkenyloxy group, a lower alkanoyl group, a lower alkanoyloxy group, a cycloalkyl group, a cycloalkyl lower alkyl group, a halogen atom, a carbamoyl group which may have a lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, an amino group which may have a lower alkanoyl group, a nitro group, a hydroxy lower alkyl group, an amino lower alkyl group which may have a lower alkyl group, a thienyl group, a saturated 3- to 8-membered heteromonocyclic group containing 1 to 2 nitrogen atoms-substituted lower alkyl group and an oxo group; R.sub.2 represents a hydrogen atom or a lower alkyl group; and A represents --O-A.sub.1- (wherein A.sub.1 represents an alkylene group which may be substituted with a hydroxy group (wherein one oxygen atom may replace a carbon of the alkylene chain) or a lower alkenylene group) or a lower alkylene group; provided that when A represents a lower alkylene group, the ring Q represents a bicyclic group selected from the group consisting of: ##STR00178## (wherein the carbon-carbon-bond represents a single bond or a double bond)] or a salt thereof.

2. The heterocyclic compound of the formula (I) according to claim 1, wherein the ring Q represents a bicyclic group selected from the group consisting of: ##STR00179## (wherein the carbon-carbon bond between the 3-position and 4-position of the bicyclic heterocyclic skeleton represents a single bond or a double bond); the ring Q may have 1 to 3 substituents selected from the group consisting of a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a hydroxy group, a lower alkoxy group, a halogenated lower alkyl group, a phenyl group, a phenyl lower alkyl group, a naphthyl lower alkyl group, a phenyl lower alkoxy group, a naphthyl lower alkoxy group, a benzoyl group, a lower alkenyloxy group, a lower alkanoyl group, a lower alkanoyloxy group, a cyclo C3-C8 alkyl group, a cyclo C3-C8 alkyl lower alkyl group, a halogen atom, a carbamoyl group which may have a lower alkyl group, a caroboxy group, a lower alkoxycarbonyl group, an amino group which may have a lower alkanoyl group, a nitro group, a hydroxy lower alkyl group, an amino lower alkyl group which may have a lower alkyl group, a thienyl group and a saturated 5- to 6-membered heteromonocyclic group containing 1 to 2 nitrogen atoms-substituted lower alkyl group; and A represents --O-A.sub.1- (wherein A.sub.1 represents a C1-C6 alkylene group which may be substituted with a hydroxy group (wherein one oxygen atom may replace a carbon of the alkylene chain)), or a salt thereof.

3. The heterocyclic compound of the formula (1) according to claim 2, wherein the ring Q represents a bicyclic group selected from the group consisting of: ##STR00180## the ring Q may have 1 to 3 substituents selected from the group consisting of a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a hydroxy group, a lower alkoxy group, a halogenated lower alkyl group, a phenyl group, a phenyl lower alkyl group, a naphthyl lower alkyl group, a phenyl lower alkoxy group, a naphthyl lower alkoxy group, a benzoyl group, a lower alkenyloxy group, a lower alkanoyl group, a lower alkanoyloxy group, a cyclo C3-C8 alkyl group, a cyclo C3-C8 alkyl lower alkyl group, a halogen atom, a carbamoyl group which may have a lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, an amino group which may have a lower alkanoyl group, a nitro group, a hydroxy lower alkyl group, an amino lower alkyl group which may have a lower alkyl group, a phenyl group, a thienyl group and a pyrrolidinyl lower alkyl group; and A represents --O-A.sub.1- (wherein A.sub.1 represents a C1-C6 alkylene group which may be substituted with a hydroxy group (wherein one oxygen atom may replace a carbon of the alkylene chain)), or a salt thereof.

4. The heterocyclic compound of the formula (1) according to claim 2, wherein the ring Q represents a bicyclic group selected from the group consisting of: ##STR00181## (the ring Q may have 1 to 3 substituents selected from the group consisting of a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a hydroxy group, a lower alkoxy group, a halogenated lower alkyl group, a phenyl group, a phenyl lower alkyl group, a naphthyl lower alkyl group, a phenyl lower alkoxy group, a naphthyl lower alkoxy group, a benzoyl group, a lower alkenyloxy group, a lower alkanoyl group, a lower alkanoyloxy group, a cyclo C3-C8 alkyl group, a cyclo C3-C8 alkyl lower alkyl group, a halogen atom, a carbamoyl group which may have a lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, an amino group which may have a lower alkanoyl group, a nitro group, a hydroxy lower alkyl group, an amino lower alkyl group which may have a lower alkyl group, a thienyl group and a pyrrolidinyl lower alkyl group) or a salt thereof.

5. The heterocyclic compound of the formula (1) according to claim 1, wherein the ring Q represents a bicyclic group selected from the group consisting of: ##STR00182## (wherein the carbon-carbon bond between the 3-position and 4-position of the bicyclic heterocyclic skeleton represents a single bond or a double bond); the ring Q may have 1 to 3 substituents thereon selected from the group consisting of a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a hydroxy group, a lower alkoxy group, a halogenated lower alkyl group, a phenyl group, a phenyl lower alkyl group, a naphthyl lower alkyl group, a phenyl lower alkoxy group, a naphthyl lower alkoxy group, a benzoyl group, a lower alkenyloxy group, a lower alkanoyl group, a lower alkanoyloxy group, a cyclo C3-C8 alkyl group, a cyclo C3-C8 alkyl lower alkyl group, a halogen atom, a carbamoyl group which may have a lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, an amino group which may have a lower alkanoyl group, a nitro group, a hydroxy lower alkyl group, an amino lower alkyl group which may have a lower alkyl group, a thienyl group, a pyrrolidinyl lower alkyl group and an oxo group; and A represents a lower alkylene group, or a salt thereof.

6. The heterocyclic compound of the formula (1) according to claim 5, wherein the ring Q represents a bicyclic group selected from the group consisting of: ##STR00183## (wherein the carbon-carbon bond between the 3-position and 4-position of the bicyclic heterocyclic skeleton represents a single bond or a double bond); the ring Q may have 1 to 3 substituents selected from the group consisting of a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a hydroxy group, a lower alkoxy group, a halogenated lower alkyl group, a phenyl group, a phenyl lower alkyl group, a naphthyl lower alkyl group, a phenyl lower alkoxy group, a naphthyl lower alkoxy group, a benzoyl group, a lower alkenyloxy group, a lower alkanoyl group, a lower alkanoyloxy group, a cyclo C3-C8 alkyl group, a cyclo C3-C8 alkyl lower alkyl group, a halogen atom, a carbamoyl group which may have a lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, an amino group which may have a lower alkanoyl group, a nitro group, a hydroxy lower alkyl group, an amino lower alkyl group which may have a lower alkyl group, a thienyl group and a pyrrolidinyl lower alkyl group, or a salt thereof.

7. The heterocyclic compound of the formula (1) according to claim 3 selected from the group consisting of: (1) 7-[4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)butoxy]-1H-quinolin-2-one, (2) 7-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-1H-quinolin-2-o- ne, (3) 7-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3,4-dihydro-- 1H-quinolin-2-one, (4) 7-[4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)butoxy]-3,4-dihydro-1H-quino- lin-2-one, (5) 7-[4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)butoxy]-1-methyl-3,4-dihydro- -1H-quinolin-2-one and (6) 6-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3,4-dihydro-1H-quin- olin-2-one; or a salt thereof.

8. The heterocyclic compound of the formula (1) according to claim 4 selected from the group consisting of: (1) 7-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3,4-dihydro-2H-isoq- uinolin-1-one (2) 7-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-2-methyl-3,4-dihydr- o-2H-isoquinolin-1-one, (3) 7-[4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)butoxy]-2-methyl-3,4-dihydro- -2H-isoquinolin-1-one, (4) 7-[4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)butoxy]-3,4-dihydro-2H-isoqu- inoline-1-one, (5) 7-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-2H-isoquinolin-1-on- e and (6) 7-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-2-methyl-2- H-isoquinolin-1-one; or a salt thereof.

9. A process for producing a heterocyclic compound represented by the formula (1): ##STR00184## [wherein ring Q represented by ##STR00185## represents --NH--CH.sub.2--, --N.dbd.CH--, --CH.sub.2--NH-- or --CH.dbd.N; and the carbon-carbon bond between the 3-position and 4-position of the heterocyclic skeleton containing Z and Y represents a single bond or a double bond); the ring Q may have at least one substituent selected from the group consisting of a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a hydroxy group, a lower alkoxy group, a halogenated lower alkyl group, an aryl group, an aryl lower alkyl group, an aryl lower alkoxy group, an arylcarbonyl group, a lower alkenyloxy group, a lower alkanoyl group, a lower alkanoyloxy group, a cycloalkyl group, a cycloalkyl lower alkyl group, a halogen atom, a carbamoyl group which may have a lower alkyl group, a carboxy group, a lower alkoxycarbonyl group, an amino group which may have a lower alkanoyl group, a nitro group, a hydroxy lower alkyl group, an amino lower alkyl group which may have a lower alkyl group, a thienyl group, a saturated 3- to 8-membered heteromonocyclic group containing 1 to 2 nitrogen atoms-substituted lower alkyl group and an oxo group; R.sub.2 represents a hydrogen atom or a lower alkyl group; and A represents --O-A.sub.1- (wherein A.sub.1 represents an alkylene group which may be substituted with a hydroxy group (wherein one oxygen atom may replace a carbon of the alkylene chain) or a lower alkenylene group) or a lower alkylene group; provided that when A represents a lower alkylene group, the ring Q represents a bicyclic group selected from the group consisting of: ##STR00186## (wherein the carbon-carbon bond represents a single bond or a double bond)] or a salt thereof, characterized by comprising a reaction of a compound represented by the formula: ##STR00187## (wherein the ring Q and A are the same as defined above, and X.sub.1 represents a halogen atom or a group which causes a substitution reaction the same as in a halogen atom) or a salt thereof with a compound represented by the formula: ##STR00188## (wherein R.sub.2 is the same as defined above) or a salt thereof.
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