JPS6346754B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to novel carbostyril derivatives. The carbostyril derivative of the present invention is a novel compound that has not been described in any literature, and is represented by the following general formula (1). [In the formula, R ¹ represents a hydrogen atom, a lower alkyl group, a phenyl lower alkyl group, a lower alkenyl group, or a lower alkynyl group. R ² represents a hydrogen atom or a lower alkyl group. R ³ represents a lower alkyl group, a halogen atom or a lower alkoxy group. n represents 0 or an integer of 1 to 3. A represents a lower alkylene group that may have a hydroxyl group as a substituent. The carbon-carbon bond between the 3rd and 4th positions of the carbostyril skeleton represents a single bond or a double bond. ] Each group shown in the above general formula (1) is more specifically as follows. Lower alkyl group...methyl, ethyl, propyl,
Isopropyl, butyl, tert-butyl, pentyl, hexyl groups, etc. Phenyl lower alkyl group...benzyl, 2-phenylethyl, 1-phenylethyl, 3-phenylpropyl, 4-phenylbutyl, 1,1-dimethyl-2-phenylethyl, 5-phenylpentyl, 6-phenylhexyl, 2-methyl-3 -Phenylpropyl group, etc. Lower alkylene groups that may have a hydroxyl group as a substituent: methylene, ethylene, trimethylene, 2-methyltrimethylene, 2,2-dimethyltrimethylene, 1-methyltrimethylene, methylmethylene, ethylmethylene, tetramethylene, pentamethylene , hexamethylene, 1-hydroxyethylene, 2-hydroxytrimethylene, 2-hydroxytetramethylene, 3-hydroxypentamethylene, 3-hydroxyhexamethylene groups, etc. In the above general formula (1)

Groups represented by the formula: phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-bromphenyl, 3-bromphenyl, 4- Bromphenyl, 2-iodophenyl, 4-iodophenyl, 3,5-dichlorophenyl, 2,6-dichlorophenyl, 3,4-dichlorophenyl, 3,4-difluorophenyl,
3,5-dibromophenyl, 3,4,5-trichlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 3-isopropylphenyl, 4-hexylphenyl, 3,4-dimethylphenyl, 2.5-dimethylphenyl, 3,4,5-trimethylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-ethoxyphenyl, 3- Ethoxyphenyl, 4-ethoxyphenyl, 4-isopropoxyphenyl, 4-hexyloxyphenyl, 3,4-dimethoxyphenyl,
3,4-diethoxyphenyl, 3,4,5-trimethoxyphenyl, 2,5-dimethoxyphenyl, 3-methyl-4-chlorophenyl, 2-chloro-6-methylphenyl, 2-methoxy-3- Chlorophenyl group etc. Lower alkenyl group: vinyl, allyl, 2-butenyl, 3-butenyl, 1-methylallyl, 2-pentenyl, 2-hexenyl group, etc. Lower alkynyl group...ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-
2-propynyl, 2-pentynyl, 2-hexynyl groups, etc. Halogen atoms: fluorine, chlorine, bromine and iodine atoms. Lower alkoxy groups: methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy, hexyloxy groups, etc. Representative compounds included in the carbostyryl derivative represented by the above general formula (1) are illustrated below. The 3,4-position dehydrogenated product of each compound refers to a compound in which the carbon-carbon bond between the 3- and 4-positions of the carbostyril skeleton is a double bond. Γ 5-[3-(4-(phenyl-1, 2, 5,
6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 5-{3-[4-(4-fluorophenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenant Γ 7-{3-[4-(-fluorophenyl)-
5-{3-[4-(4-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 7-{3-[4-(3-methylphenyl)-
5-{3-[4-(3-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 5-{3-[4-(2-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 7-{3-[4-(4-chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 5-{3-[4-(3-chlorophenyl)-
5-{3-[4-(2-chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 7-{3-[4-(4-bromphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 7-{3-[4-(2-methoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 5-{3-[4-(2-ethoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenase enyl)-1,2,5,6-tetrahydro-1-
pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 7-{3-[4-(3,4,5-trimethoxyphenyl)-1,2,5,6 5-{3-[4-(3,5-dimethoxyphenyl)-1,2,5 ,6-tetrahydro-1-
pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-dehydrogenated product Γ 5-{3-[4-(2,6-dichlorophenyl)-1,2,5,6-tetrahydro- 1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 5-{3-[4-(2-chloro-6-methylphenyl)-1,2,5,6- Tetrahydro
1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 7-[4-(4-phenyl-1,2,5,6
-Tetrahydro-1-pyridyl)butoxy]-
3,4-dihydrocarbostyryl and its 3,
4-position dehydrogenant Γ 5-{4-[4-(3-chlorophenyl)-
7-{4-[4-(2-chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 5-{4-[4-(4-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 5-{4-[4-(2-methoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate 7-{4-[4-(2-chloro- 6-methylphenyl)-1,2,5,6-tetrahydro-
1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 5-[2-(4-phenyl-1,2,5,6
-Tetrahydro-1-pyridyl)ethyl]-
3,4-dihydrocarbostyryl and its 3,
4-position dehydrogenate Γ 5-{2-[4-(4-chlorophenyl)-
7-{2-[4-(3-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]ethyl}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 5-{2-[4-(2-ethoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]ethyl}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 7-{2-[4-(3-chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]ethyl}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 5-{2-[4-(4-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]ethyl}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 7-{2-[4-(2-methoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]ethyl}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 5-{2-[4-(4-chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]ethyl}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenant
1,2,5,6-tetrahydro-1-pyridyl]ethoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 5-{2-[4-(2-ethoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]ethoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenant Γ 7-{3-[4-(3-fluorophenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 5-{3-[4-(3,4-dichlorophenyl) -1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 7-{3-[4-(3,4,5- trichlorophenyl)-1,2,5,6-tetrahydro-
1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 5-[5-(4-phenyl-1,2,5,6
-tetrahydro-1-pyridyl)pentyloxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate
-tetrahydro-1-pyridyl)hexyloxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 7-[3-methyl-4-(4-phenyl-
1,2,5,6-tetrahydro-1-pyridyl)butoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenase Γ 5-[3,3-dimethyl-4-(4-phenyl- 1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenase Γ 7-{3-methyl-4-[4-(2-chlorophenyl) )-1,2,5,6-tetrahydro-
1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 5-{3-[4-(3-methoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenant Γ 7-{3-[4-(4-methoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 5-{3-[4-(4-ethoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate )-1,2,5,6-tetrahydro-1-
pyridyl)propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 5-{4-[3-(4-hexyloxyphenyl)-1,2,5,6-tetrahydro-1 ―
pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-dehydrogenated product Γ 7-{3-methyl-4-[4-(2-methoxyphenyl)-1,2,5,6- Tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 5-{3-[4-(2-ethylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 7-{3-[4-(3-ethylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 5-{3-[4-(4-ethylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 7-{3-[4-isopropylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 5-{3-[4-(4-hexylphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 5-{4-[4-(4-chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 7-{4-[4-(2-fluorophenyl)
5-{4-[4-(3-fluorophenyl)
5-{4-[4-(4-fluorophenyl)
-1,2,5,6-tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 5-{4-[4-(3-methoxyphenyl)
7-{4-[4-(4-methoxyphenyl)
5-{4-[4-(2-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 7-{4-[4-(3-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 5-{4-[4-(4-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 5-{5-[4-(2-chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 7-{5-[4-(3-chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 5-{5-[4-(4-chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 7-{5-[4-(2-fluorophenyl)
-1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate )
-1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate )
-1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 5-{5-[4-(2-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 7-{5-[4-(3-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 5-{5-[4-(4-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-dehydrogenated product Γ 7-{5-[4-(2,3-dimethylphenyl) enyl)-1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate phenyl)
-1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate )
-1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate )
-1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate
1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 1-ethyl-5-[3-(4-phenyl-
1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 1-isopropyl-7-[3-(4-phenyl-1, 2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-butyl-5-[3-(4-phenyl-
1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 1-hexyl-7-[4-(4-phenyl-
1,2,5,6-tetrahydro-1-pyridyl)butoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-methyl-5-[4-(4-phenyl-
1,2,5,6-tetrahydro-1-pyridyl)butoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-methyl-7-{3-[4-(4-fluoro phenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate (2-chlorophenyl)-1,2,5,6-tetrahydro-
1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 1-methyl-7-{3-[4-(4-methylphenyl)-1,2,5,6- Tetrabidro
1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 1-methyl-5-{3-[4-(2,3-dimethylphenyl)-1,2,5 ,6-tetrahydro-1-pyridyl]propoxy}-3,4-
Dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 1-methyl-7-{3-[4-(2-methoxyphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}- 3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-methyl-5-{3-[4-(4-methoxyphenyl)-1,2,5,6-tetrahydro-1-pyridyl ] Propoxy}-3,4-dihydrocarbostyryl and its 3,4-dehydrogenated product Γ 1-allyl-5-[4-(4-phenyl-
1,2,5,6-tetrahydro-1-pyridyl)butoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenase Γ 1-crotyl-7-[3-(4-phenyl-
1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-allyl-5-{4-[3-(4-fluoro phenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate (2-fluorophenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-allyl-5-{3 -[4-(2-chlorophenyl)-1,2,5,6-tetrahydro-
1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenant Γ 1-(2-hexenyl)-7-{3-[4-
(3chlorophenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,
4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-allyl-5-{3-[4-(2-methylphenyl)-1,2,5,6-tetrahydro-
1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 1-allyl-7-{3-[4-(3,4-dimethylphenyl)-1,2, 5,6-tetrahydro-1-pyridyl]propoxy}-3,4-
Dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 1-allyl-5-{3-[4-(2-methoxyphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}- 3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-allyl-7-{3-[4-(4-methoxyphenyl)-1,2,5,6-tetrahydro-1-pyridyl ] Propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-benzyl-5-[3-(4-phenyl-
1-(2-phenylethyl)-7-[3-
(4-phenyl-1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-(6-phenylhexyl)-5-[ 3-
(4-phenyl-1,2,5,6-tetrahydro-1-pyridyl)propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-benzyl-7-{3-[4 -(2-fluorophenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-benzyl-5-{ 3-[4-(4-fluorophenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-benzyl -7-{4-[3-(2-chlorophenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1 -Benzyl-5-{4-[3-(2-methoxyphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydration Element Γ 1-benzyl-7-{4-[3-(4-methylphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4 Dehydrogenated product Γ 1-benzyl-5-{4-[3-(2,3-
dimethylphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4
-dihydrocarbostyryl and its 3,4-dehydrogenated product Γ 1-(2-propynyl)-7-[4-(4-
Phenyl-1,2,5,6-tetrahydro-1
-pyridyl)butoxy]-3,4-dihydrocarbostyryl and its 3,4-dehydrogenated product Γ 1-(2-butynyl)-5-[3-(4-phenyl-1,2,5,6-tetrahydr -1-
1-(2-hexynyl)-7-[3-(4-
Phenyl-1,2,5,6-tetrahydro-1
-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 1-(2-propynyl)-5-{3-[4-
(2-chlorophenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-
3,4-dihydrocarbostyryl and its 3,
4-position dehydrogenate Γ 1-(2-propynyl)-7-{3-[4-
(3-methylphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-
3,4-dihydrocarbostyryl and its 3,
4-position dehydrogenate Γ 1-(2-propynyl)-5-{3-[4-
(2-methoxyphenyl)-1,2,5,6-
Tetrahydro-1-pyridyl]propoxy}-
3,4-dihydrocarbostyryl and its 3,
4-position dehydrogenate Γ 6-[3-(4-phenyl-1,2,5,6
-tetrahydro-1-pyridyl)propoxy]
-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 8-{3-[4-(4-fluorophenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 6-{3-[4-(2-fluorophenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 8-{3-[4-(4-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 6-{3-[4-(3-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 8-{3-[4-(2-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 6-{3-[4-(4-chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 8-{3-[4-(3-chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 6-{3-[4-(2-chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 8-{3-[4-(4-bromphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 6-{3-[4-(2-methoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 8-{3-[4-(2-ethoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate enyl)-1,2,5,6-tetrahydro-1-
pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 8-{3-[4-(3,4,5-trimethoxyphenyl)-1,2,5,6 -tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 6-{3-[4-(2,3-dimethylphenyl)-1,2,5 ,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 8-{3-[4-(2,6-dichlorophenyl)-1,2,5 ,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 6-{3-[4-(2-chloro-6-methylphenyl)-1,2 ,5,6-tetrahydro-
1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 8-[4-(4-phenyl-1,2,5,6
-Tetrahydro-1-pyridyl)butoxy]-
3,4-dihydrocarbostyryl and its 3,
4-position dehydrogenate Γ 6-{4-[4-(3-chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 8-{4-[4-(2-chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 6-{4-[4-(4-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 8-{4-[4-(2-methoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 6-{4-[4-(2,3-dimethylphthalate) 8-{4-[4-(2-chloro- 6-methylphenyl)-1,2,5,6-tetrahydro-
1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 6-[2-(4-phenyl-1,2,5,6
-Tetrahydro-1-pyridyl)ethoxy]-
3,4-dihydrocarbostyryl and its 3,
4-position dehydrogenate Γ 8-{2-[4-(4-chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]ethoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 6-{2-[4-(3-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]ethoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenant Γ 8-{2-[4-(2-ethoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]ethoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 6-{2-[4-(3-chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]ethoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 8-{2-[4-(4-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]ethoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 6-{2-[4-(2-methoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]ethoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenant Γ 8-{2-[4-(4-chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]ethoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 6-{3-[4-(3-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 8-{2-[4-(2-ethoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]ethoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 6-{3-[4-(3-fluorophenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 8-{3-[4-(3,4-dichlorophenyl) -1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 6-{3-[4-(3,4,5- trichlorophenyl)-1,2,5,6-tetrahydro-
1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 8-[5-(4-phenyl-1,2,5,6
-tetrahydro-1-pyridyl)pentyloxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 6-{3-[4-(4-ethoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate )-1,2,5,6-tetrahydro-1-
pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-dehydrogenated product Γ 6-{3-[4-(4-hexyloxyphenyl)-1,2,5,6-tetrahydro-1 ―
pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-dehydrogenated product Γ 8-{3-methyl-4-[4-(2-methoxyphenyl)-1,2,5,6- Tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 6-{3-[4-(2-ethylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 8-{3-[4-(3-ethylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 6-{3-[4-(4-ethylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 8-{3-[4-(4-isopropylphenyl)- 1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 6-{3-[4-(4-hexylphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 8-{4-[4-(4-chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 6-{4-[4-(2-fluorophenyl)
8-{4-[4-(3-fluorophenyl)
-1,2,5,6-tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 6-{4-[4-(4-fluorophenyl)
8-{4-[4-(3-methoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 6-{4-[4-(4-methoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 8-{1-hydroxy-4-[4-(2- 6-{4-[4-(3-methylphenyl) ―
1,2,5,6-tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 8-{4-[4-(4-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 6-{5-[4-(2-chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 8-{5-[4-(3-chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 6-{5-[4-(4-chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated substance Γ 8-{5-[4-(2-fluorophenyl)
-1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate )
-1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate )
-1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 6-{5-[4-(2-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 8-{5-[4-(3-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 6-{5-[4-(4-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate )
-1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 6-{5-[4-(2-methoxyphenyl) )
-1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate )
-1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 6-{5-[4-(4-methoxyphenyl) )
-1,2,5,6-tetrahydro-1-pyridyl]pentyloxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenase
1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 1-ethyl-6-[3-(4-phenyl-
1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 1-isopropyl-8-[3-(4-phenyl-1, 2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-butyl-6-[3-(4-phenyl-
1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenant Γ 1-hexyl-8-[4-(4-phenyl-
1,2,5,6-tetrahydro-1-pyridyl)butoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenase Γ 1-methyl-6-[4-(4-phenyl-
1,2,5,6-tetrahydro-1-pyridyl)butoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 1-methyl-8-{3-[4-(4-fluoro phenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate (2-chlorophenyl)-1,2,5,6-tetrahydro-
1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-methyl-8-{3-[4-(4-methylphenyl)-1,2,5,6- Tetrahydro
1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-methyl-6-{3-[4-(2,3-dimethylphenyl)-1,2, 5,6-tetrahydro-1-pyridyl]propoxy}-3,4-
Dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-methyl-8-{3-[4-(2-methoxyphenyl)1,2,5,6-tetrahydro-
1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenant Γ 1-methyl-6-{3-[4-(4-methoxyphenyl)-1,2,5, 6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated substance Γ 1-allyl-8-[4-(4-phenyl-
1,2,5,6-tetrahydro-1-pyridyl)butoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenase Γ 1-crotyl-6-[3-(4-phenyl-
1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-allyl-8-{3-[4-(4-fluoro phenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenase (2-fluorophenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-allyl-8-{3 -[4-(2-chlorophenyl)-1,2,5,6-tetrahydro-
1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenant Γ 1-(2-hexenyl)-6-{4-[4-
(3-chlorophenyl)-1,2,5,6-tetrahydro-1-pyridyl]butoxy}-3,
4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-allyl-8-{3-[4-(2-methylphenyl)1,2,5,6-tetrahydro-1
-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-allyl-6-{3-[4-(3,4-dimethylphenyl)-1,2,5 ,6-tetrahydro-1-pyridyl]propoxy}-3,4-
Dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 1-allyl-8-{3-[4-(2-methoxyphenyl)-1,2,5,6-tetrahydro-1-pyridyl]butoxy}- 3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-allyl-6-{3-[4-(4-methoxyphenyl)-1,2,5,6-tetrahydro-1-pyridyl ] Propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-benzyl-8-[3-(4-phenyl-
1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-(2-phenylethyl)-6-[3-
(4-phenyl-1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-(6-phenylhexyl)-8- 3-
(4-phenyl-1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 1-benzyl-6-{3-[4 -(2-fluorophenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-benzyl-8-{ 3-[4-(4-fluorophenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-benzyl -6-{3-[4-(2-chlorophenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1 -Benzyl-8-{3-[4-(2-methoxyphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydration Element Γ 1-benzyl-6-{3-[4-(4-methylphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4 Dehydrogenated product Γ 1-benzyl-8-{3-[4-(2,3-
dimethylphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4
-dihydrocarbostyryl and its 3,4-dehydrogenated product Γ 1-(2-propynyl)-6-[4-(4-
Phenyl-1,2,5,6-tetrahydro-1
1-(2-butynyl)-8-[3-(4-phenyl-1,2,5,6-tetrahydro) -1-
1-(2-hexynyl)-6-[3-(4
-Phenyl-1,2,5,6-tetrahydro-
1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 1-(2-propynyl)-8-{3-[4-
(2-chlorophenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-
3,4-dihydrocarbostyryl and its 3,
4-position dehydrogenate Γ 1-(2-propynyl)-6-{3-[4-
(4-methylphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-
3,4-dihydrocarbostyryl and its 3,
4-position dehydrogenated product Γ 1-(2-propynyl)-8-{3-[4-
(2-methoxyphenyl)-1,2,5,6-
Tetrahydro-1-pyridyl]propoxy}-
3,4-dihydrocarbostyryl and its 3,
4-position dehydrogenator Γ 5-[2-hydroxy-3-(4-phenyl-1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position Dehydrogen Γ 5-{2-hydroxy-3-[4-(4-methylphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3, 4-position dehydrogenator Γ 7-{2-hydroxy-3-[4-(4-chlorophenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 5-{2-hydroxy-3-[4-(2-ethoxyphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-
Dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 7-{2-hydroxy-3-[4-(3,5
-dimethoxyphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-
3,4-dihydrocarbostyryl and its 3,
4-position dehydrogenate Γ 5-{2-hydroxy-3-[4-(2,6
-dichlorophenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,
4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 5-{2-hydroxy-3-[4-(2-chloro-4-methylphenyl)-1,2,5,6
-tetrahydro-1-pyridyl]propoxy}
-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 5-{2-hydroxy-3-[4-(3,
4,5-trimethoxyphenyl)-1,2,
5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenase Γ 1-methyl-7-[2-hydroxy-3-
(4-phenyl-1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 1-allyl-5-{2-hydroxy- 3-
[4-(4-methylphenyl)-1,2,5,
6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 1-benzyl-6-{2-hydroxy-3-
[4-(3-fluorophenyl)-1,2,5,
6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 1-(2-propynyl)-8-{2-hydroxy-3-[4-(2 -Methoxyphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 6-{2-hydroxy-3-[4-(3-methylphenyl) )-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate -chlorophenyl)1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 6-{2-hydroxy-3-[4-( 2,3
-dimethylphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,
4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 8-{2-hydroxy-3-[4-(2-methoxyphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy }-3,4-
Dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 4-Methyl-5-[3-(4-phenyl-
1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenant Γ 4-ethyl-6-[3-(4-phenyl-
1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenant Γ 4-propyl-7-[3-(4-phenyl-
1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 4-t-butyl-8-[3-(4-phenyl- 1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 4-pentyl-5-[3-(4-phenyl-
1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 4-hexyl-7-[3-(4-phenyl-
1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 4-methyl-5-{3-[4-(3-chlorophenyl) )-1,2,5,6-tetrahydro-
1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 4-methyl-6-{3-[4-(2-methoxyphenyl)-1,2,5, 6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 4-methyl-7-{3-[4-(2,3-dimethylphenyl)- 1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-
Dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 4-methyl-8-{3-[4-(4-methylphenyl)-1,2,5,6-tetrahydro-
1-Pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenant Γ 4-methyl-5-{2-hydroxy-3-
[4-(3-chlorophenyl)-1,2,5,
6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenant Γ 4-n-butyl-7-{2-hydroxy-3
―[4-(3-methylphenyl)-1,2,
5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenator Γ 4-hexyl-8-{2-hydroxy-3-
[4-(4-methoxyphenyl)-1,2,5,
6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 4-methyl-6-{2-hydroxy-3-
[4-(3,4,5-trimethoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenase Γ 1,4-dimethyl-5-[3-(4-phenyl) -1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate
-Phenyl-1,2,5,6-tetrahydro-
1-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-dehydrogenated product Γ 1-allyl-4-methyl-7-[3-(4-
Phenyl-1,2,5,6-tetrahydro-1
-pyridyl)propoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 1-(2-propynyl)-4-methyl-8-
[3-(4-phenyl-1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,
4-dihydrocarbostyryl and its 3,4-dehydrogenated product Γ 1,4-dimethyl-5-[2-hydroxy-
3-(4-phenyl-1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4
-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 5-{3-[4-(4-chlorophenyl)-
7-{3-[4-(4-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenant Γ 7-{3-[4-(4-fluorophenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 6-{3-[4-(2,4-dimethylphenyl) 1-(3-methylbutyl)-5-{3- [4
-(3-methylphenyl)-1,2,5,6-
Tetrahydro-1-pyridyl]propoxy}-
3,4-dihydrocarbostyryl and its 3,
4-position dehydrogenator Γ 1-allyl-5-[4-(3-methylphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4 Position dehydrogenator Γ 1-benzyl-5-{3-[4-(3-methylphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3 , 4-position dehydrogenated Γ 1-(3-phenylpropyl)-5-{3-
[4-(3-methylphenyl)-1,2,5,
6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 6-[6-(4-phenyl-1,2,5,6
-tetrahydro-1-pyridyl)hexyloxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate
1,2,5,6-tetrahydro-1-pyridyl)butoxy]3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 6-[3,3-dimethyl-4-(4-phenyl-1 ,2,5,6-tetrahydro-1-pyridyl)butoxy]-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenant Γ 8-{3-methyl-4-[4-(2-chlorophenyl) -1,2,5,6-tetrahydro-
1-pyridyl]butoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenated product Γ 6-{3-[4-(3-methoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate Γ 8-{3-[4-(4-methoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl and its 3,4-position dehydrogenate The compound of the present invention can be produced by various methods, but the preferred method is For example, it is produced by the method shown in the following reaction scheme-1. [In the formula, X represents a halogen atom, an alkanesulfonyloxy group, and an arylsulfonyloxy group represents an aralkylsulfonyloxy group. R ¹ , R ² .R ³ ,
The carbon bonds between n, A and the 3rd and 4th positions of the carbostyl skeleton are the same as above. ] That is, the compound represented by general formula (2) has general formula (3)
It is produced by reacting a known 1,2,5,6-tetrahydropyridyl derivative represented by: The above reaction is completed in a few hours to about 24 hours at a temperature of room temperature to 200°C, preferably 60 to 120°C, without a solvent or in a common inert solvent. Examples of inert solvents include dioxane, tetrahydrofuran (THF), ethers such as ethylene glycol dimethyl ether, benzene, toluene,
Aromatic hydrocarbons such as xylene, lower alcohols such as methanol, ethanol, and isopropanol, and polar solvents such as dimethylformamide (DMF) and dimethyl sulfoxide (DMSO) can be used. The above reaction is more advantageously carried out using a basic compound as a deoxidizing agent. Examples of the basic compound include tertiary amines such as potassium carbonate, sodium carbonate, sodium hydroxide, sodium bicarbonate, sodium amide, sodium hydride, triethylamine, tripropylamine, pyridine, and quinoline. The above reaction may be carried out by adding an alkali metal iodide compound such as potassium iodide or sodium iodide as a reaction promoter, if necessary. General formula for the above reaction
The ratio of the compound represented by (2) and the compound represented by general formula (3) is usually 1 to 5 times the molar amount of the latter to the former, preferably 1 to 5 times the molar amount, and more preferably 1 to 1.2 times the latter. It is said to be twice the mole. Here, the lower alkanesulfonyloxy group represented by Examples include oxy groups, and examples of arylsulfonyloxy groups include phenylsulfonyloxy, 4-methylphenylsulfonyloxy, 2-methylphenylsulfonyloxy, 4-methylphenylsulfonyloxy, and 4-methylphenylsulfonyloxy.
Examples include substituted or unsubstituted arylsulfonyloxy groups such as -nitrophenylsulfonyloxy, 4-methoxyphenylsulfonyloxy, 3-chlorophenylsulfonyloxy, and α-naphthylsulfonyloxy groups, and as aralkylsulfonyloxy groups. Specifically, benzylsulfonyloxy, 2-phenylethylsulfonyloxy,
4-phenylbutylsulfonyloxy, 4-methylbenzylsulfonyloxy, 2-methylbenzylsulfonyloxy, 4-nitrobenzylsulfonyloxy, 4-methoxybenzylsulfonyloxy, 3-chlorobenzylsulfonyloxy, α
Examples include substituted or unsubstituted aralkylsulfonyloxy groups such as naphthylmethylsulfonyloxy groups. Further, the compound of the present invention is produced by the method shown in the following reaction scheme-2. [In the formula, R ¹ , R ² , R ³ , A, n, X and the carbon-carbon bonds at the 3- and 4-positions of the carbostyril skeleton are the same as above. ] That is, the compound of the present invention is produced by reacting a hydroxycarbostyryl derivative represented by general formula (4) with a compound represented by general formula (5). The reaction conditions in the above method may be the same as those in the reaction of reaction scheme-1 described above. General formula used in the above reaction scheme-2
A new compound exists among the compounds represented by (5). These can be easily produced, for example, by the method shown in Reaction Scheme 3 below. [In the formula, X ¹ represents a halogen atom, an alkanesulfonyloxy group, an arylsulfonyloxy group, or an aralkylsulfonyloxy group. R ³ ,A,
n and X are the same as above. ] That is, a compound represented by general formula (5) is produced by reacting a compound represented by general formula (6) with a compound represented by general formula (3). The reaction conditions in the above method are the reaction scheme-1 described above.
It should be the same as that of the reaction. Further, among the compounds of the present invention, compounds in which R ¹ represents a lower alkyl group, a phenyl lower alkyl group, a lower alkenyl group, or a lower alkynyl group (compounds of general formula (1b)) are as shown in the following reaction scheme-4: Compounds in which R ₁ represents a hydrogen atom (general formula (1a)
It can also be produced by reacting a compound represented by general formula (7) with a compound represented by formula (7). [In the formula, R ¹ ' represents a lower alkyl group, phenyl lower alkyl group, lower alkenyl group, or lower alkynyl group, and X ² represents a halogen atom. ^R2 ,
R ³ , A, n and the 3rd and 4th positions of the carbostyril skeleton
The carbon-carbon bond with the position is the same as above. ] The reaction between the compound of general formula (1a) and the compound of general formula (7) is preferably carried out, for example, in the presence of a basic compound in a suitable solvent. Examples of the basic compound include sodium hydride, potassium, sodium, sodium amide, potassium amide, and the like. Examples of the solvent include ethers such as dioxane and diethylene glycol dimethyl ether, aromatic hydrocarbons such as toluene and xylene, dimethylformamide, dimethyl sulfoxide, and hexamethylphosphoric triamide. The ratio of the compound of general formula (1a) and the compound of general formula (7) to be used is not particularly limited and may be appropriately selected within a wide range, but usually the latter is at least equimolar to the former, preferably It is preferable to use about equimolar to twice the molar amount.
The reaction is usually carried out at about -50 to 70°C, preferably -30°C.
The reaction is carried out at ~room temperature, and generally completes in about 0.5 to 12 hours. [In the formula, A' represents a lower alkylene group. R ¹ , R ² ,
R ³ , n and the carbon-carbon bonds at the 3rd and 4th positions of the carbostyryl skeleton are the same as above. ] Reaction equation 6 [In the formula, X ³ is a halogen atom, Y is a group

[Formula] or group

[Formula] is shown respectively. R ¹ , R ² , R ³ , n and the carbon-carbon bonds at the 3- and 4-positions of the carbostyryl skeleton are the same as above. ] In Reaction Scheme-5, the reaction between the compound of general formula (4) and the compound of general formula (8) is carried out in a suitable inert solvent at room temperature to 200°C, preferably 50 to 120°C. , usually completed within a few hours to 24 hours. Examples of inert solvents used in the above reaction include ethers such as dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether, aromatic hydrocarbons such as benzene, triene, and xylene, lower alcohols such as methanol, ethanol, and isopropanol, dimethylformamide, and dimethyl Polar solvents such as sulfoxides can be mentioned.
Further, in the above reaction, a common basic compound can be added as necessary. Examples of the basic compound include potassium carbonate, sodium carbonate, sodium hydride, sodium hydrogen carbonate,
Examples include inorganic basic compounds such as sodium amide and sodium hydride, and tertiary amines such as triethylamine, tripropylamine, pyridine, and quinoline. The proportion of each raw material to be used may be appropriately selected within a wide range without any particular limitation, but usually the general formula (4)
The amount of the compound represented by general formula (8) relative to the compound represented by formula (8) is from equimolar to excess, preferably from equimolar to 2
Used in twice the molar amount. In reaction scheme 6, the reaction between the compound represented by the general formula (4) and the epihalohydrin represented by the general formula (9) is carried out using an appropriate basic compound such as sodium hydroxide, potassium hydroxide, sodium carbonate, or carbonate. In the presence of inorganic basic compounds such as potassium, sodium methoxide, sodium ethoxide, sodium hydroxide, metallic sodium, metallic potassium, and sodium amide, or organic basic compounds such as piperidine, pyridine, and triethylamine, without solvent or with methanol or ethanol. , lower alcohols such as isopropanol, acetone,
It is carried out in a solvent such as Kents such as methyl ethyl Kent, ethers such as ether, dioxane and diethylene glycol methyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, and water. The amount of the compound represented by the general formula (9) to be used in the reaction can be appropriately selected within a wide range, but it is usually equimolar to excess amount, preferably 5 to 10 times the amount of the compound represented by the general formula (4). The reaction proceeds at a temperature of 0 to 150°C, preferably 50 to 100°C. In the above reaction, the epihalogenohydrin represented by the general formula (9) reacts with the hydroxyl group of the compound represented by the general formula (4), usually converting the compound into a (2,3 epoxy)propoxy group or a 3-halogenohydrin. Provides a 2-hydroxypropoxy group. Generally, the reaction product is obtained as a mixture of these. The reaction product thus obtained can be reacted as a mixture with the 1,2,5,6-tetrahydropyridyl derivative represented by the general formula (3) without any particular separation and purification, or by a commonly used purification method. For example, a compound having a 2,3-epoxypropoxy group or a compound having a 3-halogeno-2-hydroxypropoxy group is separated and purified by applying a fractional recrystallization method, column chromatography, etc., and each of these is converted into a general formula. 1, 2, represented by (3)
It is also possible to react with 5,6-tetrahydropyridine derivatives. The reaction between the compound of general formula (10) and the compound of general formula (3) may be carried out in the same manner as the reaction between the compound of general formula (4) and the compound of general formula (8). Furthermore, among the carbostyril derivatives represented by the general formula (1) of the present invention, compounds in which the carbon-carbon bond between the 3rd and 4th positions of the carbostyryl skeleton are double bonds,
It can also be obtained by dehydrogenating a compound in which the above bond is a single bond, and conversely, a compound in which the above bond is a single bond can be obtained by subjecting a compound in which the above bond is a double bond to a catalytic reduction reaction. You can earn money even if you lose it. Furthermore, among the compounds of the present invention represented by the general formula (1), compounds in which R ¹ represents a hydrogen atom and the carbon bonds at the 3- and 4-positions of the carbostyril skeleton are double bonds can be expressed by the following reaction scheme-7. As shown in Figure 2, lactam-lactim tautomerism is possible. [In the formula, R ² , R ³ , n and A are the same as above. ] The carbostyril derivative represented by the general formula (1) of the present invention obtained as described above can be easily converted into an acid addition salt by acting with a pharmaceutically acceptable acid. This acid addition salt is also included. In the above, examples of acids include hydrochloric acid,
Inorganic acids such as sulfuric acid, phosphoric acid, and hydrobromic acid; organic acids such as acetic acid, oxalic acid, succinic acid, maleic acid, fumaric acid, malic acid, tartaric acid, citric acid, malonic acid, methanesulfonic acid, and benzoic acid. Can be used. Further, among the carbostyryl derivatives represented by the general formula (1) of the present invention, a compound having an acidic group can be easily formed into a salt by reacting with a pharmaceutically acceptable basic compound. Examples of the basic compound include sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium hydrogen carbonate, and the like. The target compounds obtained in each step can be easily isolated and purified by conventional separation means. Examples of the separation means include solvent extraction, dilution, recrystallization, column chromatography, preparative thin layer chromatography, and the like. Incidentally, the present invention naturally also includes optical isomers. The compound of the present invention has an excellent central nervous system depressing effect, and for example, in suppressing fighting behavior in mice isolated for long periods of time, it shows stronger efficacy than diazepane, which is known as one of the most excellent compounds in the past. Therefore, it can be advantageously used as an anxiolytic drug and an antimanic-depressant drug. Furthermore, the compound of the present invention has the effect of suppressing pain induced by acetic acid, and also has the effect of lowering body temperature and lowering blood pressure, and is useful as an antipyretic agent, an antihypertensive agent, and the like. Furthermore, the compounds of the present invention exhibit almost no anticholinergic effect, are free from the risk of side effects such as thirst, constipation, and tachycardia that are associated with conventionally known central nervous system depressants, and are acutely toxic. is also noticeably low. In addition, the compound of the present invention has antihistamine action, and is effective against various diseases caused by the binding between histamine and histamine receptors, such as sneezing, nasal discharge,
Allergy symptoms in the respiratory tract such as itching of the eyes, nose and throat, hay fever, hay fever, acute acne (itching, edema, redness, etc.), angioedema, pruritus, atopic dermatitis, insect stings, sumac rash, etc. It is useful as a therapeutic or prophylactic agent for allergic diseases such as contact dermatitis, serum sickness, allergic rhinitis, allergic conjunctivitis, and keratitis. Furthermore, the compound of the present invention has a strong anti-vapaminergic effect and a weak epinephrine suppressing effect, and is useful as a central nervous system depressant with a weak sedative effect. The compounds of the present invention can be administered to animals and humans as such or together with conventional pharmaceutical carriers.
The dosage unit form is not particularly limited and can be appropriately selected and used as required. Examples of such dosage unit forms include tablets, granules, oral preparations such as oral solutions, and parenteral preparations such as injections. The amount of the active ingredient to be administered is not particularly limited and can be appropriately selected from a wide range, but in order to achieve the desired effect, it should be 40 μg to 20 mg per kg of body weight per day.
It is best to administer in one to several divided doses. Further, it is preferable that the dosage unit form contains 1 to 500 mg of the active ingredient. In the present invention, oral preparations such as tablets, capsules, and oral solutions are manufactured according to conventional methods. For example, tablets are formed by mixing the compound of the invention with conventional pharmaceutical excipients such as gelatin, starch, lactose, magnesium stearate, talc, gum acacia, and the like. Capsules are prepared by mixing the compound of the present invention with an inert pharmaceutical filler or diluent, and filling the mixture into hard gelatin capsules, soft capsules, and the like. In addition, parenteral preparations such as injections are manufactured according to conventional methods. That is, a drug for parenteral administration is prepared by dissolving or suspending the compound of the present invention in a sterile liquid carrier. The preferred carrier is water or saline. Reference examples, examples, and formulation examples are listed below. Reference example 24 g of 1-bromo-3-chloropropane and 15 g of triethylamine were mixed in 100 ml of dimethylformamide, and 4-phenyl-1,
Gradually add 16 g of 2,5,6-tetrahydropyridine. After the dropwise addition was completed and stirred at room temperature for 8 hours,
The reaction solution was poured into 300 ml of saturated saline and extracted twice with 100 ml of chloroform. After washing the chloroform layer with water and then dehydrating it with dry sodium sulfate,
Chloroform was distilled off, and the residue was purified by silica gel column chromatography to obtain 4-
Phenyl-1-(3-chloropropyl)-1,
18 g of 2,5,6-tetrahydropyridine is obtained. Example 1 2.0 g of 7-(3-chloropropoxy)-3,4-dihydrocarbostyryl and 1.6 sodium iodide
g was mixed with 60 ml of acetone, stirred at 40-50°C for 2 hours, 60 ml of dimethylformamide was added, and the acetone was distilled off under reduced pressure. 4-phenyl-1,2,5,6-tetrahydropyridine was added to this reaction solution.
Add 1.6g and 2ml of triethylamine, 50-60
Stir at ℃ for 6 hours. Concentrate under reduced pressure to 80ml of residue.
Add a 5% aqueous solution of sodium hydrogen carbonate and stir to crystallize the organic matter. Remove the precipitate, wash with water,
Dry and recrystallize twice from ethanol, melting point
1.9 g of 7-[3-(4-phenyl-1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl is obtained in the form of colorless needle-like crystals at 157-159°C. Elemental analysis value (as C ₂₃ H ₂₆ O ₂ N ₂ ) C H N Calculated value (%) 76.21 7.23 7.73 Actual value (%) 76.06 7.17 7.66 Using appropriate starting materials. The following compound is obtained in the same manner as in Example 1. Note that the solvent in parentheses is a recrystallization solvent. Γ 5-[3-(4-phenyl 1,2,5,6-
Tetrahydro-1-pyridyl)propoxy]-
3,4-dihydrocarbostyryl Colorless needle crystals mp.201-202℃ (ethanol) Γ 5-{3-[4-(3-methylphenyl)
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless needle crystals mp.174-175℃ (ethanol) Γ 5-{3-[4-(4-methylphenyl) )
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless needle crystals mp.191-192℃ (methanol) Γ 5 {3-[4-(4-chlorophenyl) 1,
2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless needle crystals mp.193-194℃ (ethanol) Γ 5-{3-[4-(2-methoxyphenyl) )
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless needle crystals mp.155℃ (ethanol-methanol) Γ 5-{3-[4-(4-fluoro phenyl)
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless needle crystals mp.179-180℃ (ethanol-methanol) Γ 7-{3-[4-(3 -methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless scaly crystals mp.143-145℃ (ethanol-water) Γ 7-{3-[4-(4 -methylphenyl)
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless needle crystals mp.137-138℃ (ethanol-water) Γ 7-{3-[4-(4 -chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless prismatic crystal mp.184-185℃ (ethanol-methanol) Γ 7-{3-[4-(-2 methoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless scaly crystals mp.153℃ (isopropanol-water) Γ 7-{3-[4-(4- fluorophenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Pale yellow needle crystals mp.152-153℃ (ethanol) Γ 6-{3-[4-(2 ,4-dimethylphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless needle crystals mp.158-160℃ (ethanol) Γ 6-{3 -[4-(3-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-carbostyryl Colorless needle crystals mp.218℃ (ethanol-chloroform) Γ 8-{3-[4-(4-fluorophenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}carbostyryl Colorless prismatic crystals mp.163℃ (isopropanol) Γ 5-{4-[4-(4-fluorophenyl)
-1,2,5,6-tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl Colorless prismatic crystals mp.162-163℃ (ethanol) Γ 1-methyl-5-[3-(4 -Phenyl-
1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl Colorless needle crystals mp.97-98℃ (ligroin) Γ 1-(3-methylbutyl)-5-{3 ―[4
-(3-methylphenyl)1,2,5,6-tetrahydro-1-pyridyl]propoxy}-
3,4-dihydrocarbostyryl monooxalate Colorless needle crystals mp.204℃ (ethanol-water) Γ 1-allyl-5-{3-[4-(3-methylphenyl))1,2,5,6 -Tetrahydro-
1-Pyridyl}-3,4-dihydrocarbostyryl}1 oxalate Colorless needle crystals mp.209-210℃ (decomposition) (ethanol-water) Γ 1-(2-propynyl)-5-{3-[4 ―
(3-methylphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-
3,4-dihydrocarbostyryl monooxalate Colorless needle crystals mp.204-250℃ (decomposition) (ethanol-water) Γ 1-benzyl-5-{3-[4-(3-methylphenyl)-1, 2,5,6-tetrahydro-1-pyridyl]propoxy-3,4-dihydrocarbostyryl Colorless prismatic crystals mp.86-87℃ (ligroin) Γ 1-(3-phenylpropyl)-5-{3-
[4-(3-methylphenyl)-1,2,5,
6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl monooxalate colorless scaly crystals mp・202℃ (ethanol-water) Γ 1-allyl-5-[2-hydroxy-3-
(4-phenyl-1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl Colorless needle crystals mp.103-105℃ (ligroin) Γ 1-(2-propynyl) -5-{2-hydroxy-3-[4-(4-fluorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless needle crystals mp.111-113℃ (benzene-ligroin) Γ 6-{2-hydroxy-3-[ 4-(3-methoxyphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-
Dihydrocarbostyryl Colorless prismatic crystals mp.132-134℃ (ethanol) Γ 7-{2-hydroxy-3-[4-(4-chlorophenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy }-3,4-dihydrocarbostyryl Colorless needle crystals mp.169-171℃ (ethanol) Γ 1-methyl-6-{2-hydroxy-3-
[4-(3-methylphenyl)-1,2,5,
6-tetrahydro-1-pyridyl]propoxy}-carbostyryl Colorless prismatic crystals mp.100-105℃ (ethanol) Γ 4-methyl-7-[2-hydroxy-3-
(4-phenyl-1,2,5,6-tetrahydro-1-pyridyl)propoxy]-carbostyryl Colorless needle crystals mp.225-228℃ (methanol) Γ 8-{2-hydroxy-3-[4- 2,4-
dimethylphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4
-Dihydrocarbostyryl monooxalate Colorless prismatic crystals mp.215-219℃ (ethanol-water) Γ 4-methyl-7-{2-hydroxy-3-
[4-(2,4-dimethylphenyl)-1,2,
5,6-Tetrahydro-1-pyridyl]propoxy}carbostyryl monohydrochloride Colorless needle crystals mp.293-295℃ (methanol water) Γ 6-{3-[4-(3-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-carbostyryl Colorless needle crystals mp.218℃ (ethanol-chloroform) Γ 4-methyl-6-[3-(4-phenyl-)
1,2,5,6-tetrahydro-1-pyridyl]carbostyryl Colorless needle crystals mp.243-246℃ (methanol) Γ 4-methyl-6-{3-[4-(4-chlorophenyl)-1, 2,5,6-tetrahydro-
1-Pyridyl]propoxy}-carbostyryl monohydrochloride Colorless needle crystals mp.275-278℃ (decomposition) (methanol) Γ 4-methyl-7-{3-[4-(3-methylphenyl)-1, 2,5,6-tetrahydro-
1-Pyridyl]propoxy}carbostyryl Colorless needle crystals mp.192-193℃ (methanol) Γ 6-[3-(4-phenyl-1,2,5,6
-tetrahydro-1-pyridyl)propoxy]
Carbostyryl monohydriodide Colorless needle crystals mp.276-279℃ (decomposition) (methanol-water) Γ 8-{3-[4-(4-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl)propoxy}-3,4-dihydrocarbostyryl Colorless prismatic crystals mp.105-109℃ (ligroyl) Γ 1-methyl-6-{3-[4- (4-fluorophenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-carbostyryl Colorless prismatic crystals mp.114-115℃ (benzene-ligroin) Γ 6-{3-[4 -(2,4-dimethylphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-carbostyryl. 1 Hydroiodide Yellow needle crystals mp.289-292℃ (methanol-water) Example 2 5-(3-chloropropoxy)-3,4-dihydrocarbostyryl 2.0g and sodium iodide 1.6
Mix 60 ml of isopropanol and add 40 to 50 g.
After stirring at °C for 2 hours, 2.6 g of 4-(3,4,5-trimethoxyphenyl)-1,2,5,6-tetrahydropyridyl and 2.0 g of DBU were added, and the mixture was heated under reflux for 6 hours. Add the reaction solution to 5% sodium hydrogen carbonate.
Pour into 150ml and stir for 1 hour. Insoluble substances are removed, washed with water, dried, and then dissolved in acetone to obtain oxalate. Recrystallized from ethanol, melting point 210
~214℃, white crystals of 5-{3-[4-(3,4,
5-trimethoxyphenyl)-1,2,5,6-
Tetrahydro-1-pyridyl]propoxy}-
2.2 g of 3,4-dihydrocarbostyryl is obtained. Elemental analysis value (as C ₂₆ H ₃₂ N ₂ O ₅ (COOH) ₂ ) C H N Calculated value (%) 61.98 6.32 5.16 Actual value (%) 61.77 6.53 5.30 Example 3 7-Hydroxy-3,4-dihydrocarbo Styryl 3.2g, 1-chloro-3-[4-(4-methylphenyl)-1,2,5,6-tetrahydro-
1-pyridyl propane 3.5g and crushed potassium carbonate
Disperse 3.0g in 80ml dimethylformamide,
Stir at 60-70°C for 10 hours. The reaction solution was concentrated under reduced pressure, 80 ml of water was added to the residue, stirred for 2 hours, and the insoluble materials were removed, washed with water, and dried. Ethanol - recrystallized from water, melting point 137-138℃, colorless needle-like crystals.
{3-[4-(4-methylphenyl)-1,2,
2.9 g of 5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl are obtained. Elemental analysis value (as C ₂₄ H ₂₈ O ₂ N ₂ ) C H N Calculated value (%) 76.56 7.50 7.44 Actual value (%) 76.24 7.59 7.39 Using appropriate starting materials, the following compound was prepared in the same manner as in Example 3. obtain. Γ 5-[3-(4-phenyl-1,2,5,6
-tetrahydro-1-pyridyl)propoxy]
-3,4-dihydrocarbostyryl Colorless needle crystals mp.201-202℃ (ethanol) Γ 5-{3-[4-(3-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless needle crystals mp.174-175℃ (ethanol) Γ 5-{3-[4-(4-methylphenyl) )―
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless needle crystals mp.191-192℃ (ethanol) Γ 5-{3-[4-(4-chlorophenyl) )―
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless needle crystals mp.193-194℃ (ethanol) Γ 5-{3-[4-(2-methoxy) phenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless needle crystals mp.155℃ (ethanol-methanol) Γ 5-{3-[4-fluorophenyl )-1,
2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless needle crystals mp.179-180℃ (ethanol-methanol) Γ 7-[3-(4-phenyl-1, 2, 5, 6
-tetrahydro-1-pyridyl)propoxy]
-3,4-dihydrocarbostyryl Colorless needle crystals mp.157-159℃ (ethanol) Γ 7-{3-[4-(3-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless scaly crystals mp.143-145℃ (ethanol-water) Γ 7-{3-[4-(4 -chlorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless prismatic crystal mp.184-185℃ (ethanol-methanol) Γ 7-{3-[4-(2- methoxyphenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless scaly crystals mp.153℃ (isopropanol-water) Γ 7-{3-[4-(4- fluorophenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Pale yellow needle crystals mp.152-153℃ (ethanol) Γ 6-{3-[4-(2 ,4-dimethylphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless needle crystals mp.158-160℃ (ethanol) Γ 6-{3 -[4-(3-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}carbostyryl Colorless needle crystals mp.218℃ (ethanol-chloroform) Γ 8-{3-[4-(4-fluorophenyl)
-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-carbostyryl Colorless prismatic crystals mp.163℃ (isopropanol) Γ 5-{4-[4-(4-fluorophenyl)
-1,2,5,6-tetrahydro-1-pyridyl]butoxy}-3,4-dihydrocarbostyryl Colorless prismatic crystals mp.162-163℃ (ethanol) Γ 1-methyl-5-[3-(4 -Phenyl-
1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl Colorless needle crystals mp.97-98℃ (ligroyl) Γ 1-(3-methylbutyl)-5-{3 ―[4
-(3-methylphenyl)-1,2,5,6-
Tetrahydro-1-pyridyl]propoxy}-
3,4-dihydrocarbostyryl monooxalate Colorless needle crystals mp.204℃ (ethanol-water) Γ 1-allyl-5-{3-[4-(3-methylphenyl)-1,2,5,6 -Tetrahydro-
1-Pyridyl]propoxy}-3,4-dihydrocarbostyryl monooxalate Colorless needle crystals mp.209-210℃ (decomposition) (ethanol-water) Γ 1-(2-propynyl)-5-{3- [4-
(3-methylphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-
3,4-dihydrocarbostyryl monooxalate Colorless needle crystals mp.204-205℃ (decomposition) (ethanol-water) Γ 1-benzyl-5-{3-[4-(3-methylphenyl)-1, 2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless prismatic crystals mp.86-87℃ (ligroin) Γ 1-(3-phenylpropyl)-5-{3 ―
[4-(3-methylphenyl)-1,2,5,
6-Tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl monooxalate Colorless scaly crystals mp.202℃ (ethanol-water) Γ 1-allyl-5-[2-hydroxy-3-
(4-phenyl-1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl Colorless needle crystals mp.103-105℃ (ligroin) Γ 1-(2-propynyl) -5-{2-hydroxy-3-[4-(4-fluorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless needle crystals mp.111-113℃ (benzene-ligroin) Γ 6-{2-hydroxy-3-[ 4-(3-methoxyphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-
Dihydrocarbostyryl Colorless prismatic crystals mp.132-134℃ (ethanol) Γ 7-{2-hydroxy-3-[4-(4-chlorophenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy }-3,4-dihydrocarbostyryl Colorless needle crystals mp.169-171℃ (ethanol) Γ 1-methyl-6-{2-hydroxy-3-
[4-(3-methylphenyl)-1,2,5,
6-Tetrahydro-1-pyridyl]propoxy}carbostyryl Colorless prismatic crystal mp.100-105℃ (ethanol) Γ 4-Methyl-7-[2-hydroxy-3-
(4-phenyl 1,2,5,6-tetrahydro-1-pyridyl)propoxy]-carbostyryl Colorless needle crystals mp.225-228℃ (methanol) Γ 8-{2-hydroxy-3-[4-( 2,4
-dimethylphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,
4-Dihydrocarbostyryl monooxalate Colorless prismatic crystals mp.215-219℃ (ethanol-water) Γ 4-methyl-7-{2-hydroxy-3-
[4-(2,4-dimethylphenyl)-1,2,
5,6-Tetrahydro-1-pyridyl]propoxy}-carbostyryl monohydrochloride Colorless needle crystals mp.293-295℃ (methanol-water) Γ 6-{3-[4-(3-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-carbostyryl Colorless needle crystals mp.218℃ (ethanol-chloroform) Γ 4-methyl-6-[3-(4-phenyl-)
1,2,5,6-tetrahydro-1-pyridyl)propoxy]-carbostyryl Colorless needle crystals mp.243-246℃ (methanol) Γ 4-methyl-6-{3-[4-(4-chlorophenyl) -1,2,5,6-tetrahydro-
1-Pyridyl]propoxy}-carbostyryl monohydrochloride Colorless needle crystals mp.275-278℃ (decomposition) (methanol) Γ 4-methyl-7-{3-[4-(3-methylphenyl)-1, 2,5,6-tetrahydro-
1-Pyridyl]propoxy}-carbostyryl Colorless needle crystals mp.192-193℃ (methanol) Γ 6-[3-(4-phenyl-1,2,5,6
-tetrahydro-1-pyridyl)propoxy]
Carbostyryl monohydriodide Yellow needle crystals mp.276-279℃ (decomposition) (methanol-water) Γ 8-{3-[4-(4-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless prismatic crystals mp.105-109℃ (ligroin) Γ 1-methyl-6-{3-[4- (4-fluorophenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-carbostyryl Colorless prismatic crystals mp.114-115℃ (benzene-ligroin) Γ 6-{3-[4 -(2,4-dimethylphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-carbostyryl monohydriodide Yellow needle crystals mp.289-292℃ (methanol- water) Example 4 5-{3-[4-(3-methylphenyl)-
1,2,5,6-tetrahydro-1-pyridyl]
Propoxy}-3,4-dihydrocarbostyryl
1.8g and 0.26g sodium hydride (50% oil-based)
was mixed with 30 ml of dimethylformamide and stirred at room temperature for 2 hours, then 1.1 g of 1-bromo-3-methylbutane was added and stirred at room temperature for 8 hours. The reaction solution was poured into 120 ml of saturated saline solution, and the organic layer was extracted with chloroform. Wash the chloroform layer with water,
After dehydration, chloroform is distilled off, the resulting residue is purified by silica gel column chromatography, and then dissolved in acetone to obtain oxalate. Ethanol - Recrystallized from water to give colorless needle-like crystals of 1-(3-methylbutyl)-5-{3-, melting point 204℃.
[4-(3-methylphenyl)-1,2,5,6
-Tetrahydro-1-pyridyl]propoxy}-
3,4-dihydrocarbostyryl 1-oxalate 1.5
get g. Elemental analysis value (as C ₂₉ H ₃₈ O ₂ N ₂ (COOH) ₂ ) C H N Calculated value (%) 69.38 7.51 5.22 Actual value (%) 69.51 7.44 5.08 Proceed as in Example 4 using appropriate starting materials. The following compound is obtained. Γ 1-allyl-5-{3-[4-(3-methylphenyl)-1,2,5,6-tetrahydro-
1-Pyridyl]propoxy}-3,4-dihydrocarbostyryl. 1-oxalate colorless needle crystals mp.209-210℃ (decomposition) (ethanol-water) Γ 1-(2-propynyl)-5-{3-[4-
(3-methylphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-
3,4-dihydrocarbostyryl monooxalate Colorless needle crystals mp.204-205℃ (decomposition) (ethanol-water) Γ 1-benzyl-5-{3-[4-(3-methylphenyl)1,2 ,5,6-tetrahydro-
1-Pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless prismatic crystals mp.86-87℃ (ligroin) Γ 1-(3-phenylpropyl)-5-{3-
[4-(3-methylphenyl)-1,2,5,
6-Tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl monooxalate Colorless scaly crystals mp.202℃ (ethanol-water) Γ 1-methyl-5-[3-(4-phenyl-)
1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl Colorless needle crystals mp.97-98℃ (ligroin) Γ 1-allyl-5-[2-hydroxy-3 ―
(4-phenyl-1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl Colorless needle crystals mp.103-105℃ (ligroin) Γ 1-(2-propynyl) -5-{2-hydroxy-3-[4-(4-fluorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless needle crystals mp.111-113℃ (benzene-ligroin) Γ 1-methyl-6-{2-hydroxy -3-
[4-(3-methylphenyl)-1,2,5,
6-tetrahydro-1-pyridyl]propoxy}-carbostyryl Colorless prismatic crystals mp.103-105℃ (ethanol) Γ 1-methyl-6-{3-[4-(4-fluorophenyl)-1,2 ,5,6-tetrahydro-1-pyridyl]propoxy}-carbostyryl Colorless prismatic crystals mp.114-115℃ (benzene-ligroin) Example 5 7-(2,3-epoxypropoxy)-3,4
-2.2 g of dihydrocarbostyryl, 2.0 g of 4-(4-chlorophenyl)-1,2,5,6-tetrahydropyridine monohydrochloride, and 2 ml of triethylamine are mixed in 80 ml of ethanol and heated under reflux for 6 hours. Concentrate the reaction solution under reduced pressure, and add 50 ml of the residue to the
Add a 50% aqueous sodium hydrogen carbonate solution, crystallize with stirring, take the resulting crude crystals, wash with water, and then dry. When recrystallized from ethanol, melting point 169
-171℃, colorless needle crystals of 7-{2-hydroxy-
3-[4-(4-chlorophenyl)-1,2,
2.2 g of 5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl are obtained. Elemental analysis value (as C ₂₃ H ₂₅ N ₂ O ₃ Cl) C H N Calculated value (%) 66.90 6.10 6.78 Actual value (%) 66.87 6.14 6.72 The following compound was prepared in the same manner as in Example 5 using appropriate starting materials. get. Γ 1-allyl-5-[2-hydroxy-3-
(4-phenyl-1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl Colorless needle crystals mp.103-105℃ (ligroin) Γ 1-(2-propynyl) -5-{2-hydroxy-3-[4-(4-fluorophenyl)-
1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,4-dihydrocarbostyryl Colorless needle crystals mp.111-113℃ (benzene-ligroin) Γ 6-{2-hydroxy-3-[ 4-(3-methoxyphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxyto-3,4-
Dihydrocarbostyryl Colorless prismatic crystals mp.132-134℃ (ethanol) Γ 1-methyl-6-{2-hydroxy-3-
[4-(3-methylphenyl)-1,2,5,
6-Tetrahydro-1-pyridyl]propoxy}carbostyryl Colorless prismatic crystals mp.103-105℃ (ethanol) Γ 4-Methyl-7-[2-hydroxy-3-
(4-phenyl-1,2,5,6-tetrahydro-1-pyridyl)propoxy]-carbostyryl Colorless needle crystals mp.225-228℃ (methanol) Γ 8-{2-hydroxy-3-[4- (2,4
-dimethylphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}-3,
4-Dihydrocarbostyryl monooxalate Colorless prismatic crystals mp.215-219℃ (ethanol-water) Γ 4-methyl-7-{2-hydroxy-3-
[4-(2,4-dimethylphenyl)-1,2,
5,6-Tetrahydro-1-pyridyl]propoxy}-carbostyryl monohydrochloride Colorless needle crystals mp.293-295℃ (ethanol-water) Example 6 1-Methyl-6-(2,3-epoxypropoxy ) 2.3 g of carbostyril and 1.8 g of 4-(3-methylphenyl)-1,2,5,6-tetrahydropyridyl are mixed in 60 ml of ethyl acetate and heated under reflux for 5 hours. The reaction solution was concentrated under reduced pressure, extracted with chloroform, the chloroform layer was washed with water, dehydrated, the chloroform was distilled off, the residue was crystallized with ether, and the resulting crude crystals were recrystallized from ethanol, with a melting point of 100-105°C. , colorless prismatic crystal 1
-Methyl-6-{2-hydroxy-3-[4-
2.4 g of (3-methylphenyl)-1,2,5,6-tetrahydro-1-pyridyl]propoxy}carbostyryl is obtained. Elemental analysis value (as C ₂₅ H ₂₈ N ₂ O ₃ ) C H N Calculated value (%) 74.23 6.98 6.93 Actual value (%) 74.19 6.93 6.97 Formulation example 1 Tablets with the following composition in each tablet were manufactured in the usual manner. did. 7-[3-(4-phenyl-1,2,5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl 5mg Corn starch 132mg Magnesium stearate 18mg Lactose 45mg Total 200mg Formulation example 2 Ordinary Tablets having the following composition in one tablet were manufactured by the method. 5-[3-(4-phenyl-1,2, 5,6-tetrahydro-1-pyridyl)propoxy]-3,4-dihydrocarbostyryl 10mg Corn starch 127mg Magnesium stearate 18mg Lactose 45mg Total 200mg

Claims (1)

[Claims] 1. General formula [In the formula, R ¹ represents a hydrogen atom, a lower alkyl group, a phenyl lower alkyl group, a lower alkenyl group, or a lower alkynyl group. R ² represents a hydrogen atom or a lower alkyl group. R ³ represents a lower alkyl group, a halogen atom or a lower alkoxy group. n represents 0 or an integer of 1 to 3. A represents a lower alkylene group that may have a hydroxyl group as a substituent. The carbon-carbon bond between the 3rd and 4th positions of the carbostyril skeleton represents a single bond or a double bond. ] A carbostyryl derivative represented by these and its salt.