Patent CA-2169737-A1 (CA)
Inventor: ISHIKAWA KIYOFUMI
IPC: C07D419/04
Filed: 1994-08-16
Abstract: A heteroaromatic ring-fused cyclopentene derivative of the formula:       (I) wherein each  of  Ar1  and Ar2  is  independently  a  phenyl group,  a thienyl group,  a pyridyl group, an  indolyl group,  a benzofuranyl  group or  a dihydrobenzofuranyl group  wherein  an  optional  hydrogen  atom(s)  on  the aromatic  ring  may  be  replaced with  1  to  4  groups selected from the group consisting of a halogen atom, a hydroxyl group,  an amino group,  a carboxyl  group,  a C1-C6  alkoxycarbonyl  group,  a  mono-  or  di-  C1-C6 alkylaminocarbonyl   group,   a   carbamoyl   group,   a tetrazol-5-yl  group,  a methylenedioxy  group,  a  C1-C6 alkoxy group, a C2-C6 alkenyloxy group, a mono- or di-C1-C6  alkylamino group,  a C1-C6  alkyl  group,  a C2-C6 alkenyl group and a C2-C6 alkynyl group (provided that the C1-C6 alkoxy group, C2-C6 alkenyloxy group, mono- or di-  C1-C6  alkylamino  group,  C1-C6  alkyl  group,  C2-C6 alkenyl group and C2-C6 alkynyl group may be substituted by 1 to 3 groups selected from the group consisting of a phenyl group, a pyridyl group, an imidazolyl group,  a hydroxyl group, a C1-C6 alkoxy group, an amino group, a mono- or di- C1-C6  alkylamino group,  a hydroxy C1-C6 alkylcarbonyl group, a C1-C6 acyloxy C1-C6 alkylcarbonyl group, a carboxy C1-C6 alkoxycarbonyl group, a carboxy C1-C6 alkoxycarbonyl C1-C6 alkoxycarbonyl group, a C1-C6 alkoxycarbonyl  group,  a  mono-  or  di- C1-C6  alkyl-aminocarbonyl  group,   a  carbamoyl  group,   a  C1-C6 alkylsulfonylaminocarbonyl group, a tetrazol-5-ylamino-carbonyl  group,  a  carboxyl  group,  SO3H,  PO3H2,  a tetrazol-5-yl    group,    a    2-oxo-3H-1,2,3,5-oxathia-diazol-4-yl  group  and  a  5-oxo-4H-1,2,4-oxadiazol-3-yl group  (provided  that  when  a  hydroxyl  group  and  a carboxyl group are selected as substituents,  they may together form a lactone ring)); each of R1, R2 and R3 is independently a hydrogen atom, a hydroxyl group or a C1-C6 alkyl group, or R1 and R2, or R2 and R3 together form a single bond;    Y is a group of -CO-R4  (wherein R4 is a hydroxyl group, an amino group, a C1-C6 alkoxy group, a mono- or di- C1-C6 alkylamino group,  a C1-C6 alkylsulfonylamino group, or an arylsulfonylamino group or an aryl C1-C6 alkylsulfonylamino group wherein an optional hydrogen atom(s) on the aryl ring may be replaced with a C1-C6 alkyl  group),  SO3H,  PO3H2,  a  tetrazol-5-yl  group,  a 2-oxo-3H-1,2,3,5-oxathiadiazol-4-yl    group    or    a 5-oxo-4H-1,2,4-oxadiazol-3-yl group; and A is a group which forms together with the adjacent carbon-carbon  double  bond  a  5-  or  6-  membered heteroaromatic  ring  including  1  to  4  hetero  atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom (provided that optional 1 or 2 hydrogen atoms on the heteroaromatic ring may be replaced with a hydroxyl group, an amino group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a halogen atom, a cyano  group,  a  nitro  group,  a  mono-  or  di-  C1-C6 alkylamino group which may be substituted by a hydroxyl group at the alkyl moiety, a C3-C8 cycloalkylamino group which may be substituted by a hydroxyl group at the alkyl  or  alkylene  moiety,  a  C3-C8  cycloalkyl  C1-C6 alkylamino group which may be substituted by a hydroxyl group  at  the  alkyl  or  alkylene  moiety,  an  N-(C1-C6 alkyl)-N-(C3-C8  cycloalkyl)amino  group  which  may  be substituted by a hydroxyl group at the alkyl or alkylene moiety,  an N-(C1-C6  alkyl)-N-(aroyl)amino group which may be substituted by a hydroxyl group at the alkyl moiety,  a  C4-C7  cyclic  imino  group  which  may  be substituted by a hydroxyl group at the alkylene moiety, a carboxyl group, a C1-C6 alkoxycarbonyl group, a formyl group,  a C2-C6  alkanoyl group,  an aroyl group,  or  a C1-C6  alkyl  group,   C3-C8  cycloalkyl  group,   C3-C8 cycloalkyl C1-C6 alkyl group,   C2-C6 alkenyl group or C2-C6 alkynyl group which may be substituted by 1 to 3 substituents selected from the group consisting of  a hydroxyl group, an amino group, a C1-C6 alkoxy group and a mono-  or di- C1-C6  alkylamino group,  and when the heteroaromatic ring includes one or more nitrogen atoms, the nitrogen atom(s) may be oxidized to form an N-oxide group); or a pharmaceutically acceptable salt thereof.