Carbostyril derivatives

• US 5,006,528 A
• Filed: 10/20/1989
• Issued: 04/09/1991
• Est. Priority Date: 10/31/1988
• Status: Expired due to Term

• Current Assignee: Otsuka Pharmaceutical Company Limited (Otsuka Holdings Company Limited)
• Original Assignee: Otsuka Pharmaceutical Company Limited (Otsuka Holdings Company Limited)
• Inventors: Sato, Seiji, Oshiro, Yasuo, Kurahashi, Nobuyuki
• Primary Examiner(s): Waddell, Frederick E.
• Assistant Examiner(s): TURNIPSEED, JAMES
• Application Number:
  US07/424,719
• Time in Patent Office: 536 Days
• Field of Search: 544/363, 514/253
• US Class Current: 514/253.07
• CPC Class Codes: C07D 215/227 only one oxygen atom which is attached in position 2

Abstract

A novel carbostyril derivative and salt thereof represented by the formula (1) ##STR1## (wherein R is a group of the formula ##STR2## ((wherein R¹ is a C_1- C₃ alkoxy group)), a group of the formula ##STR3## ((wherein R² and R ³ are each, at the same time, a chlorine atom, a bromine atom; and R⁴ is a hydrogen atom or a chlorine atom)), 2-methyl-3-nitrophenyl group, 3,5-dichlorophenyl group, or a group of the formula ##STR4## ((wherein R⁵ is a chlorine atom or a bromine atom; and R⁶ is a methyl group)); the carbon-carbon bond between 3- and 4-position in the carbostyril skeleton is a single or double bond).

Claims

1. A carboxtyril compound or salt thereof of the formula, ##STR34## wherein R is a group of the formula ##STR35## wherein R¹ is a C₁ -C₃ alkoxy group;

a group of the formula ##STR36## wherein R² and R³ are at the same time, both chlorine atoms, or both bromine atoms and R⁴ is a hydrogen atom or a chlorine atom;

a 2-methyl-3-nitrophenyl group;

a 3,5-dichlorophenyl group;

or a group of the formula ##STR37## wherein R⁵ is a chlorine atom or a bromine atom and R⁶ is a methyl group;

the carbon-carbon bond between the 3- and 4-positions in the carboxtyril skeleton being a single or a double bond.

2. The carboxtyril compound or salt thereof of claim 1, wherein R is a group of the formula ##STR38##

3. The carboxtyril compound or salt thereof of claim 2, wherein R¹ is a methoxy group or an ethoxy group.

4. The carboxtyril compound or salt thereof of claim 1, wherein R is a group of the formula ##STR39##

5. The carbostyril compound or salt thereof of claim 4, wherein R² and R³ are chlorine atoms and R⁴ is a hydrogen atom.

6. The carbostyril compound or salt thereof of claim 4, wherein R² and R³ are bromine atoms and R⁴ is a hydrogen atom.

7. The carbostyril compound or salt thereof of claim 4, wherein R², R³ and R⁴ are chlorine atoms.

8. The carbostyril compound or salt thereof of claim 1, wherein R is a 2-methyl-3-nitrophenyl group or a 3,5-dichlorophenyl group.

9. The carbostyril compound or salt thereof of claim 1, wherein R is a group of the formula ##STR40##

10. The carbostyril compound or salt thereof of claim 9, wherein R⁵ is a chlorine atom.

11. The carbostyril compound or salt thereof of claim 9, wherein R⁵ is a bromine atom.

16. A pharmaceutical composition for treating schizophrenia containing, as the active ingredient, a carbostyril compound or pharmaceutically acceptable salt thereof of claim 1 and a pharmaceutically acceptable carrier.

17. The pharmaceutical composition of claim 16, wherein the carbostyril compound or salt thereof is 7-{4-[4-(2,3-dichlorophenyl)-1-piperazinyl]butoxy}-3,4-dihydrocarbostyril.

18. The pharmaceutical composition of claim 16, wherein the carbostyril compound or salt thereof is 7-{4-[4-(2,3-dichlorophenyl)-1-piperazinyl]butoxy}carbostyril.

19. The pharmaceutical composition of claim 16, wherein the carbostyril compound or salt thereof is 7-{4-[4-(2-ethoxyphenyl)-1-piperazinyl]butoxy}-3,4-dihydrocarbostyril.

20. The pharmaceutical composition of claim 16, wherein the carbostyril compound or salt thereof is 7-{4-[4-(2-ethoxyphenyl)-1-piperazinyl]butoxy}carbostyril.

21. The pharmaceutical composition for treating schizophrenia containing, as the active ingredient, a carbostyril compound or pharmaceutically acceptable salt thereof of claim 3 and a pharmaceutically acceptable carrier.

12. 7-{4-[4-(2,3-Dichlorophenyl)-1-piperazinyl]butoxy}-3,4-dihydrocarbostyril.

13. 7-{4-[4-(b 2,3-Dichlorophenyl)-1-piperazinyl]-butoxy}carbostyril.

14. 7-{4-[4-(2-Ethoxyphenyl)-1-piperazinyl]butoxy}-3,4-dihydrocarbostyril.

15. 7-{4-[4-]2-Ethoxyphenyl)-1-piperazinyl]butoxy}-carbostyril.