Nitrogen-containing aromatic derivatives

A method of treating cancer comprising administering a compound represented by the formula:

• or a pharmacologically acceptable salt thereof;
• wherein:
• R1 and R2 are each independently a hydrogen atom, an optionally substituted C1-6 alkyl group, an optionally substituted C2-6 alkenyl group, an optionally substituted C2-6 alkynyl group, an optionally substituted C3-8 alicyclic hydrocarbon group, an optionally substituted C2-7 acyl group or an optionally substituted C2-7 alkoxycarbonyl group;
• Z12 is a hydrogen atom, an optionally substituted C1-6 alkyl group, an optionally substituted C2-6 alkenyl group, an optionally substituted C2-6 alkynyl group, an optionally substituted C3-8 alicyclic hydrocarbon group, an optionally substituted C6-14 aryl group, an optionally substituted 5- to 14-membered heterocyclic group, an optionally substituted 5- to 14-membered aromatic heterocyclic group or a group represented by the formula:
• wherein Z31, Z33 and Z34 are each independently a methylene group, —CO—, —NH— or —O—, and Z32 is a single bond, a methylene group, —CO—, —NH— or —O—;
• and
• wherein Z12 is not pyrazolyl;
• Ya1 is a group represented by the formula:
• wherein W31 and W32 are each independently an optionally substituted carbon atom or a nitrogen atom;
• R300 and R301 are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, an amino group, an optionally substituted C1-6 alkyl group, an optionally substituted C3-8 alicyclic hydrocarbon group, an optionally substituted C1-6 alkoxy group, an optionally substituted C2-7 alkoxycarbonyl group, a formyl group, a group represented by the formula
• wherein V300 and V301 are each independently a hydrogen atom or an optionally substituted C1-6 alkyl group, or an optionally substituted C2-7 acyl group;
• Ra11 is a group represented by the formula —Va21—Va22—Va23, wherein:
• Va21 is an optionally substituted C1-6 alkylene group, a single bond or a group represented by the formula:
• Va22 is a single bond, an oxygen atom, a sulfur atom, —CO—, —SO—, —SO2—, —CONRa14—, —SO2NRa14—, —NRa14SO2—, —NRa14CO— or —NRa14—;
• wherein Ra14 is a hydrogen atom, an optionally substituted C1-6 alkyl group or an optionally substituted C3-8 alicyclic hydrocarbon group;
• and
• Va23 is a hydrogen atom, an optionally substituted C1-6 alkyl group, an optionally substituted C2-6 alkenyl group, an optionally substituted C2-6 alkynyl group, an optionally substituted C3-8 alicyclic hydrocarbon group, an optionally substituted C6-14 aryl group, an optionally substituted 5- to 14-membered heterocyclic group or an optionally substituted 5- to 14-membered aromatic heterocyclic group;
• and
• Ra12 is a cyano group or a group represented by the formula:
• wherein:
• Va11 is —CO— or —SO2—;
• and
• Va12, Va13 and Va14 are each independently a hydrogen atom, an optionally substituted C1-6 alkyl group, an optionally substituted C2-6 alkenyl group, an optionally substituted C2-6 alkynyl group, an optionally substituted C3-8 alicyclic hydrocarbon group, an optionally substituted C6-14 aryl group, an optionally substituted 5- to 14-membered heterocyclic group or an optionally substituted 5- to 14-membered aromatic heterocyclic group;
• with the exception that the compound is not:
• (1) a compound wherein Ra12 is a group represented by the formula:
• wherein:
• Va12 and Va13 are each independently a hydrogen atom, an optionally substituted C1-6 alkyl group, an optionally substituted C2-6 alkenyl group, an optionally substituted C2-6 alkynyl group, an optionally substituted C3-8 alicyclic hydrocarbon group, an optionally substituted C6-14 aryl group, an optionally substituted 5- to 14-membered heterocyclic group or an optionally substituted 5- to 14-membered aromatic heterocyclic group;
• R1 and R2 are hydrogen atoms;
• and
• Z12 is a C6-14 aryl group, a 6- to 14-membered heterocyclic group or a 6- to 14-membered aromatic heterocyclic group;
• or
• (2) a compound wherein Ra12 is a group selected from the group consisting of the formulae:
• wherein:
• Va11 is —CO— or —SO2—;
• Va12, Va13 and Va14 are each independently a hydrogen atom, an optionally substituted C1-6 alkyl group, an optionally substituted C2-6 alkenyl group, an optionally substituted C2-6 alkynyl group, an optionally substituted C3-8 alicyclic hydrocarbon group, an optionally substituted C6-14 aryl group, an optionally substituted 5- to 14-membered heterocyclic group or an optionally substituted 5- to 14-membered aromatic heterocyclic group;
• R2 is a hydrogen atom;
• and
• Z12 is (a) a C6-14 aryl group, (b) a 5- to 14-membered heterocyclic group, (c) a 5- to 14-membered aromatic heterocyclic group, (d) a C1-6 alkyl group substituted with a 5- to 10-membered heterocyclic group or a C5-10 alicyclic hydrocarbon group, (e) a C2-6 alkenyl group substituted with a 5- to 10-membered heterocyclic group or a C5-10 alicyclic hydrocarbon group, (f) a C2-6 alkynyl group substituted with a 5- to 10-membered heterocyclic group or a C5-10 alicyclic hydrocarbon group, or (g) a C3-8 alicyclic hydrocarbon group substituted with a 5- to 10-membered heterocyclic group or a C5-10 alicyclic hydrocarbon group,
• or a pharmacologically acceptable salt thereof.