US 2009/0023716 A1Published application

Benzoxazines and Related Nitrogen-Containing Heterobicyclic Compounds Useful as Mineralocorticoid Receptor Modulating Agents

AssigneeMitsubishi Tanabe Pharma Corporation

InventorsToru Iijima, Yasuo Yamamoto, Hidenori Akatsuka, Takayuki Kawaguchi

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Abstract

The present invention relates to a compound, useful as a mineralocorticoid receptor-modulating agent, of the following formula [I]: wherein Ring A is a benzene ring optionally having a substituent(s) other than R1 etc, R1 is a group of the formula: RaSO2NH— etc, Ra is an alkyl group etc, R2 and R3 are each a hydrogen atom, a phenyl group, an optionally substituted alkyl group etc, X is an oxygen atom etc, Y is a group of the formula: —C(═O)— etc, Ar is an optionally substituted aryl group or an optionally substituted heteroaryl group, Q is a single bond, an alkylene group etc, or a pharmaceutically acceptable salt thereof.

Claims24

Dependent claims

A compound of the following formula [I]:

wherein Ring A is a benzene ring optionally having a substituent(s) other than R1 or a nitrogen-containing 6-membered aromatic heterocyclic ring optionally having a substituent(s) other than R1,
R1 is a group of the formula:
RaSO2NH—, RaSO2NH—CH2— or (Rb)(Rc)NSO2—,
Ra is an alkyl group, a cycloalkyl group, an amino group optionally substituted by an alkyl group(s), an optionally substituted aryl group, or an optionally substituted heteroaryl group,
Rb and Rc are the same or different and are each a hydrogen atom, an alkyl group or a cycloalkyl group,
R2 and R3 are the same or different and are each a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an alkenyl group, a carboxyl group, an alkoxycarbonyl group, an optionally substituted carbamoyl group or an optionally substituted aryl group, or both R2 and R3 combine each other together with the adjacent carbon atom to form a saturated or unsaturated cyclic group (said cyclic group optionally containing the same or different one or two heteroatom(s) selected from an oxygen atom, a sulfur atom and a nitrogen atom),
X is an oxygen atom, a sulfur atom, a methylene group or a group of the formula:
—NR4—,
R4 is a hydrogen atom, an alkyl group, an optionally substituted aralkyl group or an acyl group,
Y is a group of the formula:
—C(═O)—, —C(═S)— or —CH(R5)—,
R5 is a hydrogen atom, an alkyl group or an optionally substituted aryl group,
Ar is an optionally substituted aryl group or an optionally substituted heteroaryl group, and
Q is a single bond, an alkylene group or an alkenylene group, or a pharmaceutically acceptable salt thereof
excluding
N-(4-benzyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)(p-toluenesulfonamide);
N-[4-(2-fluorobenzyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl][4-(N-acetylamino)benzenesulfonamide];
N-[4-(4-fluorobenzyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl][4-(N-acetylamino)benzenesulfonamide];
N-[4-(7-amidinonaphthalen-2-yl)methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]benzenesulfonamide;
N-[4-(7-amidinonaphthalen-2-yl)methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl](p-methoxyphenylsulfonamide);
N-[4-(7-amidinonaphthalen-2-yl)methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl](6-bromonaphthalene-2-yl)sulfonamide;
N-[4-(7-amidinonaphthalen-2-yl)methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl] (5-quinolylsulfonamide);
and
N-[2,2-dimethyl-4-(1-oxidopyridin-2-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]methanesulfonamide.

21 more elements

A compound of the following formula [I-a]:

wherein Ring A is a benzene ring optionally having a substituent(s) other than R11 or a nitrogen-containing 6-membered aromatic heterocyclic ring optionally having a substituent(s) other than R11,
R11 is a group of the formula:
RaaSO2NH—, RaaSO2NH—CH2— or (Rb)(Rc)NSO2—,
Raa is an alkyl group, a cycloalkyl group, an amino group optionally substituted by one or two alkyl group(s), a phenyl group or a 5- or 6-membered monocyclic heteroaryl group,
Rb and Rc are the same or different and are each a hydrogen atom, an alkyl group or a cycloalkyl group,
one of R21 and R31 is a hydrogen atom, a halogen atom or an alkyl group, and another is a hydrogen atom, an alkyl group, an alkoxycarbonyl group, a phenyl group or a halogenophenyl group, or both of them combine each other together with the adjacent carbon atom to form a saturated or unsaturated cyclic group (said cyclic group optionally containing the same or different one or two heteroatom(s) selected from an oxygen atom, a sulfur atom and a nitrogen atom),
Xa is an oxygen atom, a sulfur atom, a methylene group or a group of the formula:
—NH—,
Ya is a group of the formula:
—C(═O)—, —C(═S)— or —CH(R51)—,
R51 is a hydrogen atom or a phenyl group,
Ar1 is
(a) a phenyl (or naphthyl) group optionally substituted by one to three group(s) selected from a halogen atom, a hydroxyl group, a cyano group, a nitro group, an alkyl group optionally substituted by one to three halogen atom(s), a hydroxyalkyl group, an acyloxyalkyl group, an alkoxy group optionally substituted by one to three halogen atom(s), an alkoxycarbonylalkoxy group, an alkylthio group, an alkylenedioxy group optionally substituted by one to two halogen atom(s), an amino group optionally substituted by one or two alkyl group(s), an acylamino group, a cycloalkyl group and an alkylsulfonyl group;
(b) a thienyl group optionally substituted by one to two group(s) selected from a halogen atom and a trihalogenoalkyl group, said thienyl group being optionally fused to a benzene ring;
(c) a pyridyl group optionally substituted by one to two group(s) selected from a halogen atom, a nitro group, an alkyl group and a trihalogenoalkyl group;
(d) a pyrimidinyl group optionally substituted by a halogen atom;
(e) a quinolyl group;
(f) a pyridazinyl group optionally substituted by a halogen atom;
(g) a pyrrolyl group;
(h) a furyl group optionally fused to a benzene ring;
(i) a thiazolyl group optionally fused to a benzene ring;
or
(j) an imidazolyl group optionally fused to a benzene ring and optionally substituted by an alkyl group, and
Q is a single bond, an alkylene group or an alkenylene group,
or a pharmaceutically acceptable salt thereof.

22 more elements

A compound selected from the group consisting of:

N-(3-oxo-2,4-diphenyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-methanesulfonamide;
N-[4-(4-fluorophenyl)-3-oxo-2-phenyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-chlorophenyl)-3-oxo-2-phenyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl]-methanesulfonamide;
N-(2,2-dimethyl-3-oxo-4-phenyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-methanesulfonamide;
N-[4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]-methanesulfonamide;
N-[4-(4-chlorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]-methanesulfonamide;
N-[4-(3,4-difluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-fluoro-3-methylphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(3-chloro-4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-methoxyphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]ethanesulfonamide;
N-[4-(5-fluoropyridin-2-yl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-(4-benzyl-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-methanesulfonamide;
N-(4-benzyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)methanesulfonamide;
N-[4-(4-fluorophenyl)-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]-methanesulfonamide;
4-(4-fluorophenyl)-N,2,2-trimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-sulfonamide;
N-[4-(5-chloro-2-thienyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N′-[4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]-N,N-dimethylsulfamide;
N-[4-(4-fluorophenyl)-2,2-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl]-methanesulfonamide;
N-[2,2-dimethyl-3-oxo-4-(3-thienyl)-3,4-dihydro-2H-1,4-benzoxazin-7-yl]-methanesulfonamide;
N-[4-(4-fluorophenyl)-3-oxo-3,4-dihydrospiro[1,4-benzoxazine-2,1′-cyclobutan]-7-yl]methanesulfonamide;
N-[1-(4-fluorophenyl)-3,3-dimethyl-2-oxo-1,2,3,4-tetrahydroquinoxalin-6-yl]-methanesulfonamide;
N-[4-(4-fluoro-3-trifluoromethyl)phenyl]-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[2,2-dimethyl-4-(4-methylphenyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-fluorophenyl)-3-oxo-3,4-dihydrospiro[1,4-benzoxazin-2,1′-cyclopropan]-7-yl]methanesulfonamide;
N-[2,2-diethyl-4-(4-fluorophenyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]-methanesulfonamide;
N-[2-ethyl-4-(4-fluorophenyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]-methanesulfonamide;
N-[2,2-dimethyl-3-oxo-4-[(4-trifluoromethyl)phenyl]-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]sulfamide;
N-[4-(2,4-difluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-fluorophenyl)-2,2-dimethyl-3-thioxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-fluoro-2-methylphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-chloro-3-methoxyphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-fluoro-3-methoxyphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
4-(4-fluoro-3-methylphenyl)-N,2,2-trimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-sulfonamide;
N-[4-[3-(dimethylamino)-4-fluorophenyl]-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(3-chloro-4-fluorophenyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]-methanesulfonamide;
N-[4-(2-chloro-4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-chloro-2-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-chloro-2-methylphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-bromophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-fluorophenyl)-2,2,6-trimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[6-amino-4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-[3-(difluoromethyl)-4-fluorophenyl]-2,2-dimethyl-3-oxo-3,4-dihydro-2H 1,4-benzoxazin-7-yl]methanesulfonamide;
4-(4-chlorophenyl)-N,2,2-trimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-sulfonamide;
N-[4-(4-chloro-2-cyanophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
4-(4-bromophenyl)-N,2,2-trimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-sulfonamide;
N-[4-(5-chloropyridin-2-yl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[5-chloro-4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-bromo-2-methylphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-[4-chloro-3-(trifluoromethyl)phenyl]-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-[3-fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-chloro-3-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-chloro-3-methylphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(3-fluoro-4-methylphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
4-(4-chloro-2-methylphenyl)-N,2,2-trimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-sulfonamide;
N-[4-(2,4-dimethylphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(3-chloro-4-methylphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(3,4-difluoro-5-methoxyphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(3,4-dichlorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[2,2-dimethyl-4-(2-naphthyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]-methanesulfonamide;
N-[4-(4-fluoro-2,6-dimethylphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[5-bromo-4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(5-chloro-2-methylphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[5-chloro-4-(4-chlorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-fluorophenyl)-2,2,5-trimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-bromo-3-methylphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(2,2-difluoro-1,3-benzodioxol-5-yl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-(4-mesityl-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-methanesulfonamide;
N-[4-(2,6-dimethylphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-chloro-2,6-dimethylphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(5-bromo-3-methylpyridin-2-yl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[5-fluoro-4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(3,5-dichloropyridin-2-yl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-fluoro-2,3-dimethylphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(3-chloro-2-methylphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(5-fluoro-2-methylphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[2,2-dimethyl-3-oxo-4-(1-phenylethyl)-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[2,2-dimethyl-4-(3-methylbenzyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[2,2-dimethyl-4-[2-methyl-5-(trifluoromethyl)phenyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[2,2-dimethyl-3-oxo-4-(2,4,6-trifluorophenyl)-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
2-chloro-5-[2,2-dimethyl-7-[(methylsulfonyl)amino]-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl]benzyl benzoate;
N-[4-(4-chloro-2-methoxy-5-methylphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(6-chloro-2,2-difluoro-1,3-benzodioxol-5-yl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[2,2-dimethyl-4-(3-methyl-5-nitropyridin-2-yl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(5-chloro-3-methylpyridin-2-yl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-[4-fluoro-2-(trifluoromethyl)phenyl]-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[2,2-dimethyl-4-[2-methyl-4-(trifluoromethyl)phenyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-5-vinyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-chlorophenyl)-5-fluoro-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(5-chloropyridin-2-yl)-5-fluoro-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(3-chlorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-[5-bromo-6-methylpyridin-2-yl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[5-fluoro-4-(5-fluoropyridin-2-yl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[2,2-dimethyl-3-oxo-4-[5-(trifluoromethyl)-2-thienyl]-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(6-chloro-4-methylpyridin-3-yl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(5-bromopyridin-2-yl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-[4-chloro-3-(hydroxymethyl)phenyl]-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(6-bromo-5-methylpyridin-3-yl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide,
N-[4-(6-chloro-2-methylpyridin-3-yl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-{2,2-dimethyl-3-oxo-4-[5-(trifluoromethyl)pyridin-2-yl]-3,4-dihydro-2H-1,4-benzoxazin-7-yl}methanesulfonamide;
N-{2,2-dimethyl-4-[3-methyl-6-(trifluoromethyl)pyridin-2-yl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl}methanesulfonamide;
N-[4-(5-chloro-3-fluoropyridin-2-yl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(3-chlorophenyl)-5-fluoro-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(5-bromopyridin-2-yl)-5-fluoro-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(5-chloro-3-methylpyridin-2-yl)-5-fluoro-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-{5-fluoro-2,2-dimethyl-3-oxo-4-[5-(trifluoromethyl)pyridin-2-yl]-3,4-dihydro-2H-1,4-benzoxazin-7-yl}methanesulfonamide;
N-[4-(5-fluoro-3-methylpyridin-2-yl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(5-chloro-3-fluoropyridin-2-yl)-5-fluoro-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-[4-chloro-3-(hydroxymethyl)phenyl]-5-fluoro-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
2-chloro-5-[5-fluoro-2,2-dimethyl-7-[(methylsulfonyl)amino]-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl]benzyl benzoate;
N-[4-(2,6-dimethylpyridin-3-yl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[5-cyclopropyl-4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[5-fluoro-4-[3-fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[5-fluoro-2,2-dimethyl-3-oxo-4-[4-(trifluoromethyl)phenyl]-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[5-fluoro-4-[4-fluoro-3-(trifluoromethyl)phenyl]-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(3-chloro-4-fluorophenyl)-5-fluoro-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(3,4-difluorophenyl)-5-fluoro-2,2-di-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[5-fluoro-4-(5-fluoro-6-methylpyridin-2-yl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(6-chloro-2-methylpyridin-3-yl)-5-fluoro-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-chloro-2-fluorophenyl)-5-fluoro-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(5-fluoro-6-methylpyridin-2-yl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(benzothien-2-yl)-2,2-di-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(benzofuran-2-yl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-[2-chloro-6-(trifluoromethyl)pyridin-3-yl]-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[2,2-dimethyl-4-[3-methyl-5-(trifluoromethyl)pyridin-2-yl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[2,2-di-methyl-4-[2-methyl-6-(trifluoromethyl)pyridin-3-yl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[2,2-dimethyl-4-[2-methyl-5-(trifluoromethyl)pyridin-3-yl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[5-ethyl-4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[5-fluoro-2,2-dimethyl-3-oxo-4-[5-(trifluoromethyl)-2-thienyl]-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[5-fluoro-4-(5-fluoro-3-methylpyridin-2-yl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(6-chloro-2,2-difluoro-1,3-benzodioxol-5-yl)-5-fluoro-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(2,2-difluoro-1,3-benzodioxol-5-yl)-5-fluoro-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(5-bromo-3-methylpyridin-2-yl)-5-fluoro-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[5-fluoro-2,2-dimethyl-4-(3-methyl-5-(trifluoromethyl)pyridin-2-yl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-chloro-2-methylphenyl)-5-fluoro-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(3-amino-4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
N-[4-(4-fluoro-2-methoxyphenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide;
4-(3-chloro-4-fluorophenyl)-N,2,2-trimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-sulfonamide;
N-{2,2-dimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydro-2H-1,4-benzoxazin-7-yl}methanesulfonamide;
and
N-{2,2-dimethyl-4-[2-methyl-3-(trifluoromethyl)phenyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl}methanesulfonamide;
or a pharmaceutically acceptable salt thereof.

142 more elements

A pharmaceutical composition comprising as an active ingredient a compound of the following formula [I]:

wherein Ring A is a benzene ring optionally having a substituent(s) other than R1 or a nitrogen-containing 6-membered aromatic heterocyclic ring optionally having a substituent(s) other than R1,
R1 is a group of the formula:
RaSO2NH—, RaSO2NH—CH2— or (Rb)(Rc)NSO2—,
Ra is an alkyl group, a cycloalkyl group, an amino group optionally substituted by an alkyl group(s), an optionally substituted aryl group, or an optionally substituted heteroaryl group, Rb and Rc are the same or different and are each a hydrogen atom, an alkyl group or a cycloalkyl group,
R2 and R3 are the same or different and are each a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an alkenyl group, a carboxyl group, all alkoxycarbonyl group, an optionally substituted carbamoyl group or an optionally substituted aryl group, or both R2 and R3 combine each other together with the adjacent carbon atom to form a saturated or unsaturated cyclic group (said cyclic group optionally having the same or different one or two heteroatom(s) selected from an oxygen atom, a sulfur atom and a nitrogen atom),
X is an oxygen atom, a sulfur atom, a methylene group or a group of the formula:
—NR4, R4 is a hydrogen atom, an alkyl group, an optionally substituted aralkyl group or an acyl group,
Y is a group of the formula:
—C(═O)—, —C(═S)— or —CH(R5)—, R5 is a hydrogen atom, an alkyl group or an optionally substituted aryl group,
Ar is an optionally substituted aryl group or an optionally substituted heteroaryl group, and
Q is a single bond, an alkylene group or an alkenylene group, or a pharmaceutically acceptable salt thereof,
excluding
N-(4-benzyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)(p-toluenesulfonamide);
N-[4-(2-fluorobenzyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl][4-(N-acetylamino)benzenesulfonamide];
N-[4-(4-fluorobenzyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl][4-(N-acetylamino)benzenesulfonamide];
N-[4-(7-amidinonaphthalen-2-yl)methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]benzenesulfonamide;
N-[4-(7-amidinonaphthalen-2-yl)methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl](p-methoxyphenylsulfonamide);
N-[4-(7-amidinonaphthalen-2-yl)methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl](6-bromonaphthalene-2-yl)sulfonamide;
N-[4-(7-amidinonaphthalen-2-yl)methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl](5-quinolylsulfonamide);
and
N-[2,2-dimethyl-4-(1-oxidopyridin-2-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]methanesulfonamide.

18 more elements

A pharmaceutical composition comprising as an active ingredient a compound of the following formula [I-a]:

wherein Ring A is a benzene ring optionally having a substituent(s) other than R11 or a nitrogen-containing 6-membered aromatic heterocyclic Ting optionally having a substituent(s) other than R11,
R11 is a group of the formula:
RaaSO2NH—, RaaSO2NH—CH2— or (Rb)(Rc)NSO2—,
Raa is an alkyl group, a cycloalkyl group, an amino group optionally substituted by one or two alkyl group(s), a phenyl group or a 5- or 6-membered monocyclic heteroaryl group,
Rb and Rc are the same or different and are each a hydrogen atom, an alkyl group or a cycloalkyl group,
one of R21 and R31 is a hydrogen atom, a halogen atom or an alkyl group, and another is a hydrogen atom, an alkyl group, an alkoxycarbonyl group, a phenyl group or a halogenophenyl group, or R21 and R31 combine each other together with the adjacent carbon atom to form a saturated or unsaturated cyclic group (said cyclic group optionally containing the same or different one or two heteroatom(s) selected from an oxygen atom, a sulfur atom and a nitrogen atom),
Xa is an oxygen atom, a sulfur atom, a methylene group or a group of the formula:
—NH—,
Ya is a group of the formula:
—C(═O)—, —C(═S)— or —CH(R51)—,
R51 is a hydrogen atom or a phenyl group,
Ar1 is (a) a phenyl (or naphthyl) group optionally substituted by one to three group(s) selected from a halogen atom, a hydroxyl group, a cyano group, a nitro group, an alkyl group optionally substituted by one to three halogen atom(s), a hydroxyalkyl group, an acyloxyalkyl group, an alkoxy group optionally substituted by one to three halogen atom(s), an alkoxycarbonylalkoxy group, an alkylthio group, an alkylenedioxy group optionally substituted by one to two halogen atom(s), an amino group optionally substituted by one or two alkyl group(s), an acylamino group, a cycloalkyl group and an alkylsulfonyl group;
(b) a thienyl group optionally substituted by one to two group(s) selected from a halogen atom and a trihalogenoalkyl group, said thienyl group being optionally fused to a benzene ring;
(c) a pyridyl group optionally substituted by one to two group(s) selected from a halogen atom, a nitro group, an alkyl group and a trihalogenoalkyl group;
(d) a pyrimidinyl group optionally substituted by a halogen atom;
(e) a quinolyl group;
(f) a pyridazinyl group optionally substituted by a halogen atom;
(g) a pyrrolyl group;
(h) a furyl group optionally fused to a benzene ring;
(i) a thiazolyl group optionally fused to a benzene ring or (j) an imidazolyl group optionally fused to a benzene ring and optionally substituted by an alkyl group, and
Q is a single bond, an alkylene group or an alkenylene group,
or a pharmaceutically acceptable salt thereof.

19 more elements

Dependencies are inferred from the claim text.