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US 6,582,351 B1Granted
Imidazopyridinone derivatives and their use as phosphodiesterase inhibitors
AssigneeFujisawa Pharmaceutical Co., Ltd.
InventorsKozo Sawada, Takayuki Inoue, Yuki Sawada, Tsuyoshi Mizutani
Life of this patent
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Abstract
A compound (Ia): wherein the variables are defined in the specification, its prodrug or a pharmaceutically acceptable salt thereof useful in the treatment of angina, hypertension etc.
Claims7
A compound of the formula (Ia):
- wherein
- Xa is nitrogen atom;
- Ya is oxygen atom;
- R1a is cyano group;
- nitro group;
- carbamoyl group;
- a lower alkylcarbamoyl group which may be substituted with a heterocyclic group;
- carboxy group;
- a lower alkoxycarbonyl group;
- a lower alkyl group;
- a halo(lower)alkyl group;
- a lower alkanoyl group;
- an aroyl group;
- or a lower alkanesulfonyl group,
- R2a is a cycloalkyl group which has one to three substituents selected from the group consisting of hydroxy, acyloxy, acyl, lower-alkoxy-substituted aralkyloxy, amino, acylamino, lower alkoxycarbonylamino, lower alkanesulfonylamino, ureido, lower alkylureido, sulfamoylamino, lower alkoxycarbonyl, lower alkanesulfonyl, lower alkyl, hydroxy(lower)alkyl, acyloxy(lower)alkyl, lower alkylenedioxy, carbamoyl, and sulfamoyl;
- R3a, R4a and R5a are, the same or different, hydrogen atom, a halogen atom, a lower alkanoyl group, carboxy group, a protected carboxy group, carbamoyl group, nitro group, cyano group, a lower alkyl group optionally substituted by hydroxy, a lower alkoxy group or a lower-alkoxy-substituted aralkyl group;
- or two of R3a, R4a and R5a may combine together to form a lower alkylenedioxy group, and
- m is an integer of 1 or 2,
- its prodrug or a pharmaceutically acceptable salt thereof.
16 more elements
A process for preparing a compound of the formula (Ia):
- wherein
- Xa is nitrogen atom;
- Ya is oxygen atom;
- R1a is cyano group;
- nitro group;
- carbamoyl group;
- a lower alkylcarbamoyl group which may be substituted with a heterocyclic group;
- carboxy group;
- a lower alkoxycarbonyl group;
- a lower alkyl group;
- a halo(lower)alkyl group;
- a lower alkanoyl group;
- an aroyl group;
- or a lower alkanesulfonyl group,
- R2a is a cycloalkyl group which has one to three substituents selected from the group consisting of hydroxy, acyloxy, acyl, lower-alkoxy-substituted aralkyloxy, amino, acylamino, lower alkoxycarbonylamino, lower alkanesulfonylamino, ureido, lower alkylureido, sulfamoylamino, lower alkoxycarbonyl, lower alkanesulfonyl, lower alkyl, hydroxy(lower)alkyl, acyloxy(lower)alkyl, lower alkylenedioxy, carbamoyl, and sulfamoyl;
- R3a, R4a and R5a are, the same or different, hydrogen atom, a halogen atom, a lower alkanoyl group, carboxy group, a protected carboxy group, carbamoyl group, nitro group, cyano group, a lower alkyl group optionally substituted by hydroxy, a lower alkoxy group or a lower-alkoxy-substituted aralkyl group;
- or two of R3a, R4a and R5a may combine together to form a lower alkylenedioxy group, and
- m is an integer of 1 or 2,
- its prodrug or a pharmaceutically acceptable salt thereof, which comprises reacting a compound of the formula (IIa):
- wherein
- R1a, R2a, Xa and Ya are as defined above,
- or its salt with a compound of the formula (IIIa):
- wherein R3a, R4a, R5a and m are as defined above, and Z1 is a halogen atom, in the presence of a base.
20 more elements
Dependencies are inferred from the claim text.