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Details for Patent: 4,824,840

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Details for Patent: 4,824,840

Title: Carbostyril derivatives and pharmaceutical preparations containing same
Abstract:Carbostyril derivatives having antihistaminic action and central nervous controlling action are useful as antihistaminic agents or central nervous controlling agents. The derivatives are represented by the general formula, ##STR1## wherein R.sup.1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms or a phenylalkyl group, an alkylene group containing 1 to 4 carbon atoms; R.sup.2 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a phenyl group; R.sup.3 is a hydrogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkanoyloxy group having 1 to 4 carbon atoms or a 3,4,5-trimethoxybenzoyloxy group; R.sup.4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R.sup.5 is a cycloalkyl group having 3 to 8 carbon atoms, a phenyl group (which may have 1 to 3 substituted groups selected from the group consisting of halogen atoms, alkyl groups having 1 to 4 carbon atoms and alkoxy groups having 1 to 4 carbon atoms), an alkyl group having 1 to 4 carbon atoms (having one substituted group such as a hydroxy group, a phenyl group or an alkanoyloxy group having 1 to 4 carbon atoms), an alkanoyl group having 1 to 4 carbon atoms or benzoyl group; X is a halogen atom; n is 0, or an integer of 1 or 2; Q is an integer of 2 or 3, l and m are respectively an integer of 0 to 1-6, but the sum of l and m should not exceed 6; the carbon-carbon bond at the 3- and 4-positions in the carbostyril skeleton is a single or double bond and; the substituted position of the side chain of ##STR2## is any one of the 4-, 5-, 6-, 7- or 8-positions.
Inventor(s): Banno; Kazuo (Tokushima, JP), Fujioka; Takafumi (Tokushima, JP), Oshiro; Yasuo (Tokushima, JP), Nakagawa; Kazuyuki (Tokushima, JP)
Assignee: Otsuka Pharmaceutical Co., Ltd. (JP)
Filing Date:Mar 12, 1987
Application Number:07/025,193
Claims:1. A carbostyril derivative represented by the formula, ##STR25## wherein R.sup.1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms or a phenyl alkyl group having an alkylene group having 1 to 4 carbon atoms; R.sup.2 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a phenyl group; R.sup.3 is a hydrogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkanoyloxy group having 1 to 4 carbon atoms or a 3,4,5-trimethoxybenzoyloxy group; R.sup.4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R.sup.5 is a cycloalkyl group having 3 to 8 carbon atoms, a phenyl group which may be substituted by 1 to 3 identical or different groups selected from the group consisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a substituted alkyl group having 1 to 4 carbon atoms, having one hydroxy group, phenyl group or alkanoyloxy group having 1 to 4 carbon atoms as the substituent, an alkanoyl group having 1 to 4 carbon atoms and a benzoyl group; X is a halogen atom; n is 0 or an integer of 1 or 2; Q is an integer of 3; l and m are respectively 0 or an integer of 1 to 6, but the sum of l and m should not exceed 6; the carbon-carbon bond at the 3- and 4-positions in the carbostyril skeleton is a single or double bond; the substituted position of the side chain of ##STR26## is any one of the 4-, 5-, 6-, 7- or 8-positions, or a pharmaceutically acceptable acid addition salt thereof, with the proviso that when said side chain is substituted at the 4-position and said carbon-carbon bond at the 3- or 4-positions is a double bond, then R.sup.2 does not exist.

2. A carbostyril derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 1, wherein R.sup.3 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

3. A carbostyril derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 1, wherein R.sup.3 is a hydroxy group, an alkanoyloxy group having 1 to 4 carbon atoms or a 3,4,5-trimethoxybenzoyloxy group.

4. A carbostyril derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 2, wherein R.sup.5 is a phenyl group which may be substituted by 1 to 3 identical or different groups selected from the group consisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms and an alkoxy group having 1 to 4 carbon atoms.

5. A carbostyril derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 2, wherein R.sup.5 is a substituted alkyl group having 1 to 4 carbon atoms, having one phenyl group as the substituent.

6. A carbostyril derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 2, wherein R.sup.5 is selected from the group consisting of a cycloalkyl group having 3 to 8 carbon atoms; a substituted alkyl group having 1 to 4 carbon atoms having one hydroxy group or alkanoyloxy group having 1 to 4 carbon atoms as the substituent; an alkanoyl group having 1 to 4 carbon atoms and a benzoyl group.

7. A carbostyril derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 3, wherein R.sup.5 is a phenyl group which may be substituted by 1 to 3 identical or different groups selected from the group consisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms and an alkoxy group having 1 to 4 carbon atoms.

8. A carbostyril derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 3, wherein R.sup.5 is selected from the group consisting of a cycloalkyl group having 3 to 8 carbon atoms; a substituted alkyl group having 1 to 4 carbon atoms having one hydroxy group, phenyl group or alkanoyloxy group having 1 to 4 carbon atoms as the substituent; an alkanoyl group having 1 to 4 carbon atoms and a benzoyl group.

9. A carbostyril derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 4, wherenin the substituted position of the side chain represented by the formula, ##STR27## is the 5- or 7-position in the carbostyril skeleton.

10. A carbostyril derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 4, wherein the substituted position of the side chain represented by the formula, ##STR28## is the 4-, 6- or 8-position in the carbostyril skeleton.

11. A carbostyril derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 9, wherein the substituted position of the side chain represented by the formula, ##STR29## is the 5-position in the carbostyril skeleton.

12. A carbostyril derivative or a pharmaceutically acceptable acid addition salt thereof according to claim 9, wherein the substituted position of the side chain represented by the formula, ##STR30## is the 7-position in the carbostyril skeleton.

13. 5-[3-(4-Phenylhomopiperazinyl)propoxy]-3,4-dihydrocarbostyril.

14. A pharmaceutical composition useful as an antihistaminic agent, comprising an antihistaminically effective amount of a carbostyril derivative or a pharmaceutically acceptable salt thereof according to claim 1 and a pharamaceutically acceptable carrier.

15. A pharmaceutical composition useful as a central nervous controlling agent, comprising an amount of carbostyril derivative or a pharmaceutically acceptable acid salt thereof according to claim 1 sufficient to affect the central nervous system and a pharmaceutically acceptable carrier.
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