Pyrimidine-5-carboxamide derivatives

A pyrimidine-5-carboxamide derivative represented by a formula (I) or a salt thereof

• wherein each symbol has the following meaning;
• X:
• O;
• S;
• NR1;
• CO;
• NR1CO;
• CONR1;
• C═N—OR1 or a bond,
• Y:
• a lower alkylene group which may be substituted by OR1 or —NHR1;
• or a bond,
• Z:
• O or NR2,
• A:
• H;
• or a lower alkyl which may have from 1 to 4 substituent(s) selected from Group a or Group c;
• a —CO-lower alkyl which may have from 1 to 4 substituent(s) selected from Group a or Group c;
• an aryl which may have from 1 to 4 substituent(s) selected from Group a or Group b;
• a five- to eight-membered monocyclic heteroaryl group which (i) has from 1 to 4 hetero atoms selected from O, S, and N and (ii) may have from 1 to 4 substituent(s) selected from Group a or Group b;
• a cycloalkyl which may have from 1 to 4 substituent(s) selected from Group a;
• or a five- to eight-membered saturated heterocyclic group which (i) has at least one N as a ring atom, (ii) may have one O or S as a ring atom, and (iii) may have from 1 to 4 substituent(s) selected from Group a,
• B:
• an aryl which may have from 1 to 4 substituent(s) selected from Group a or Group b or a five- to eight-membered monocyclic heteroaryl group which (i) has from 1 to 4 hetero atoms selected from O, S, and N and (ii) may have from 1 to 4 substituent(s) selected from Group a or Group b, and
• R1, R2:
• H;
• a lower alkyl or —CO-lower alkyl group,
• Group a:
• —NH2;
• —NH2 in a prodrug form;
• -lower alkylene-NH2;
• -lower alkylene-NH2 in a prodrug form;
• —NH-lower alkyl;
• —N(lower alkyl)2;
• —NH-lower alkylene-aryl;
• —NH-aryl;
• —NH-cycloalkyl;
• —NH-a five- to eight-membered monocyclic heteroaryl group which has from 1 to 4 hetero atoms selected from O, S, and N;
• —NHCO-lower alkyl;
• —NHSO2-lower alkyl;
• —NHC(NH)NH2;
• —NHCONH2;
• —OH;
• —O-lower alkyl;
• —CO2H;
• —CONHOH;
• —CO2-lower alkyl;
• —CONH-lower alkyl;
• or —CON(lower alkyl)2,
• Group b:
• -lower alkyl;
• -halogen atom selected from the group consisting of F, Cl, Br, and I;
• -lower alkyl having One or more hydrogen atoms substituted by a halogen atom selected from the group consisting of F, Cl, Br, and I;
• —O-lower alkylene-aryl;
• —O-aryl;
• —O-lower alkylene-aryl-O-lower alkyl;
• —S-lower alkylene-aryl;
• —S-lower alkylene-aryl-O-lower alkyl;
• —NO2;
• or —CN, and
• Group c:
• -halogen atom selected from the group consisting of F, Cl, Br, and I;
• —O-lower alkylene-aryl, —O-aryl;
• —O-lower alkylene-aryl-O-lower alkyl;
• —S-lower alkylene-aryl;
• —S-lower alkylene-aryl-O-lower alkyl;
• —NO2;
• —CN;
• -aryl which may be substituted by a group selected from Group a;
• -cycloalkyl;
• -a five- to eight-membered monocyclic heteroaryl group which has from 1 to 4 hetero atoms selected from 0, S, and N;
• -a five- to eight-membered saturated heterocyclic group having from 1 to 4 hetero atoms selected from O, S, and N;
• -vinyl;
• -(1-propenyl);
• or -ethynyl,
• with the proviso that A is a group other than an ethyl group when X is NH, Y and Z are respectively a bond and B is 2-methylphenyl, and
• wherein —NH2 in the prodrug form means a group selected from the group consisting of (Z)-3-{2-(acetoxy)phenyl}-2-propenoylanino-, (acetoxy)rnethoxycarbonylamino-, 4-azidobenzyloxycarbonylamino-, (5-methyl-2-oxo-1,3-dioxol-4-en-4-yl)methoxycarbonylamino-, and {(2-hydroxyphenyl)(phenyl)methylidene}amino-.