Tetrahydroisoquinoline compound
AssigneeKowa Company, Ltd.
InventorsSeiichi Sato, Junya Tagashira, Shunji Takemura, Yoshiharu Miyake, Tetsuya Ishikawa, Toshiharu Arai, Takahiro Ito, Takuya Hara
Life of this patent
Estimating the term…
Abstract
The present invention relates a specific tetrahydroisoquinoline compound which is useful as a chemokine receptor type 3 (CCR3) antagonist, and a pharmaceutical composition comprising the same as an active ingredient. The tetrahydroisoquinoline compound of the present invention is useful for the treatment or prevention of a disease in which CCR3 participates.
Claims13
A tetrahydroisoquinoline compound represented by the following formula (1):
- or a pharmaceutically acceptable salt thereof, wherein
- R1, R2, R3, and R4, which are the same or different, each represent —H, -halogen, C1-6 alkyl which may be substituted, —OH, —O—C1-6 alkyl, —SH, —S—C1-6 alkyl, —COOH, —CO—C1-6 alkyl, —CO—O—C1-6 alkyl, —CO—NH—C1-6 alkyl, —NO2, —NH2, —NH—C1-6 alkyl, —N(C1-6 alkyl)2, or —NH—CO—C1-6 alkyl;
- R5 represents C1-6 alkyl which may be substituted, C3-10 cycloalkyl which may be substituted, C6-14 aryl which may be substituted, —C1-6 alkylene-C3-10 cycloalkyl which may be substituted, or —C1-6 alkylene-C6-14 aryl which may be substituted;
- R6 represents —H, —C1-6 alkyl which may be substituted, or —Y′-A′;
- X represents C1-6 alkylene;
- Y and Y′, which are the same or different, each represent a single bond or C1-6 alkylene;
- A and A′, which are the same or different, each represent C6-14 aryl which may be substituted or 3- to 15-membered heterocyclic group which may be substituted;
- and
- n represents 0 or 1.
A tetrahydroisoquinoline compound or a pharmaceutically acceptable salt thereof selected from:
- N-(4-tert-butylbenzyl)-2-[3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine,
- N-(3-acetylbenzyl)-2-[3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine,
- 3-[[2-[3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethylamino]methyl]-N,N-diethylbenzamide,
- N-(4-tert-butylbenzyl)-2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine,
- N-(3-acetylbenzyl)-2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine,
- N-[3-(methanesulfonylamino)benzyl]-2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine,
- N-(3,5-dimethanesulfonylaminobenzyl)-2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine,
- 4-[[2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethylamino]methyl]-N-isopropylaniline,
- 4-[[2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethylamino]methyl]-N-ethylaniline,
- N-[4-(4-morpholino)benzyl]-2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine,
- 4-[[2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethylamino]methyl]-N-(2-methoxyethyl)aniline,
- 3-[[2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethylamino]methyl]-N,N-diethylbenzamide,
- N-[4-(1-hydroxy-1-methylethyl)benzyl]-2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine,
- 3-[[2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethylamino]methyl]benzamide,
- N-(4-tert-butylbenzyl)-2-[3-(4-chlorobenzyl)-6-fluoro-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine,
- N-(3-methanesulfonylaminobenzyl)-2-[3-(4-chlorobenzyl)-6-fluoro-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine,
- 4-[[2-[7-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethylamino]methyl]-N-isopropylaniline,
- N-(pyridin-4-yl)methyl-2-[3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine, and
- N-(pyridin-4-yl)methyl-2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine.
Dependencies are inferred from the claim text.