Back to results
US 2013/0096310 A1Published application
Isoquinoline derivative
AssigneeTaisho Pharmaceutical Co., Ltd.
InventorsTetsuo Takayama, Madoka Kawamura, Daisuke Wakasugi, Rie Nishikawa, Yoshinori Sekiguchi
Life of this patent
Estimating the term…
Abstract
A compound represented by formula (I) or a pharmaceutically acceptable salt thereof has an effect of inhibiting CRTH2 and, therefore, is useful as a pharmaceutical.
Claims6
A compound represented by formula (I):
- wherein R1 represents a C1-6 alkyl group, a C2-6 alkenyl group, a C3-6 cycloalkyl group, a C3-6 cycloalkenyl group, an adamantyl group, an indanyl group, a tetrahydronaphthyl group, a tetrahydroindolyl group, a tetrahydropyranyl group, a morpholinyl group, a phenyl group, a naphthyl group, or an aromatic heterocyclic group, wherein the phenyl group, the naphthyl group, and the aromatic heterocyclic group may be substituted with 1 to 5 substituent(s) selected from the group consisting of a C1-6 alkyl group, a C2-6 alkenyl group, a C3-6 cycloalkyl group, a halogen atom, a C1-6 alkoxy group, a hydroxy group, a C1-6 alkylthio group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, a C1-6 haloalkylthio group, a cyano group, a nitro group, a guanidino group, a C1-6 alkylsulfonyl group, a carboxy group, a C2-7 alkoxycarbonyl group, a C2-7 alkanoyloxy group, a phenyl group, a benzoyl group, a phenoxy group, a pyrrolyl group, a thienyl group, an imidazolyl group, a thiadiazolyl group, a morpholino group, the formula:
- —NR5R6, the formula:
- —SO2NR7R8, the formula:
- —NR9SO2R10, the formula:
- —CONR11R12, and the formula:
- —NR13COR14, wherein R5, R6, R7, R8, R9, R10, R11, R12, R13, and R14 each independently represent a hydrogen atom or a C1-6 alkyl group;
- X represents an oxygen atom, a sulfur atom, the formula:
- —CRhRi—, the formula:
- —CO—, the formula:
- —NR2—, or formula (II):
- wherein Rh and Ri each independently represent a hydrogen atom, a C1-6 alkyl group, a halogen atom or a C1-6 haloalkyl group;
- R2 represents a hydrogen atom or a C1-6 alkyl group;
- n represents an integer of 1 to 4;
- Y represents a single bond, the formula:
- —NR3CO—W—, the formula:
- —NR3CO—W—O—, the formula:
- —NR3CO2—W—, the formula:
- —NR3—W—, the formula:
- —NR3SO2—W—, the formula:
- —NR3CONR4—W—, the formula:
- —NR3CO—W—NR4SO2—, the formula:
- —SO2NR3—W—, the formula:
- —CH2—W—, the formula:
- —CONR3—W—, the formula:
- —CONR3—W—O—, the formula:
- —CH2—O—W—, the formula:
- —CH2NR3—W—, the formula:
- —CONR3—W—NR4CO—, the formula:
- —O—W—, or the formula:
- —O—W—O—, wherein R3 and R4 each independently represent a hydrogen atom or a C1-6 alkyl group, W is a single bond, a C1-6 alkylene group, a C2-6 alkylene group including a carbon atom that is also a member of a C3-6 cycloalkyl ring, a C2-6 alkenylene group, or a C3-6 cycloalkylene group (provided that, when Y is the formula:
- —CONR3—W—NR4CO— or the formula:
- —O—W—O—, W is not a single bond);
- Z represents a benzene ring, a pyrimidine ring, or a pyrazine ring;
- said benzene ring, pyrimidine ring, and pyrazine ring may be substituted with 1 to 4 substituent(s) selected from the group consisting of a C1-6 alkyl group, a C2-6 alkenyl group, a C3-6 cycloalkyl group, a halogen atom, a C1-6 alkoxy group, a hydroxy group, a C1-6 alkylthio group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, a C1-6 haloalkylthio group, a cyano group, a nitro group, a C1-6 alkylsulfonyl group, a carboxy group, the formula:
- —NR22R23, the formula:
- —SO2NR24R25, the formula:
- —NR26SO2R27, the formula:
- —CONR28R29, and the formula:
- —NR30COR31, wherein R22, R23, R24, R25, R26, R27, R28, R29, R30, and R31 to each independently represent a hydrogen atom or a C1-6 alkyl group (provided that, when Z is an unsubstituted benzene ring, unsubstituted pyrimidine ring, or unsubstituted pyrazine ring, X is the formula:
- —CRhRi—, or formula (II), wherein at least one of Rh and Ri represents a C1-6 alkyl group, a halogen atom, or a C1-6 haloalkyl group);
- Ra represents a carboxy group, a carbamoyl group, a tetrazolyl group, or the formula:
- —CONHOH;
- Rb and Rc each independently represent a hydrogen atom, a halogen atom, or a C1-6 alkyl group;
- and
- Rd, Re, Rf and Rg each independently represent a hydrogen atom, a halogen atom, a C1-6 alkyl group, or a C1-6 alkoxy group (provided that the compound is not {1-[2-fluoro-5-(propan-2-yloxy)benzyl]-6,7-dimethoxyisoquinolin-4-yl}acetic acid, 2-[1-(2-fluoro-5-methoxybenzoyl)-6,7-dimethoxyisoquinolin-4-yl)acetamide, {1-[3-fluoro-5-(propan-2-yloxy)benzoyl]-6,7-dimethoxyisoquinolin-4-yl}acetic acid, 2-{1-[3-fluoro-5-(propan-2-yloxy)benzoyl]-6,7-dimethoxyisoquinolin-4-yl}propanoic acid, 2-{1-[2-fluoro-5-(propan-2-yloxy)benzoyl]-6,7-dimethoxyisoquinolin-4-yl}-4-methylpentanoic acid, 2-{1-[2-fluoro-5-(propan-2-yloxy)benzoyl]-6,7-dimethoxyisoquinolin-4-yl}propanoic acid, {1-[2-fluoro-5-(propan-2-yloxy)benzoyl]-6,7-dimethoxyisoquinolin-4-yl}acetic acid, or [6,7-dimethoxy-4-(1H-tetrazol-5-ylmethyl)isoquinolin-1-yl](2-fluoro-5-methoxyphenyl)methanone);
- or a pharmaceutically acceptable salt thereof.
43 more elements
Dependencies are inferred from the claim text.