Heterocyclic compounds

A process for preparing a compound of the formula:

• ##STR12## wherein X.sup.1 is C--R.sup.6,
• X.sup.2 is C--R.sup.7,
• X.sup.3 is C--R.sup.8,
• R.sup.1 is hydrogen or halogen,
• R.sup.2 is halogen,
• R.sup.3 is nitro, amino optionally having suitable substituent(s) or a heterocyclic group optionally having suitable substituent(s),
• R.sup.4 and R.sup.5 are each or halogen,
• R.sup.6 and R.sup.8 are each hydrogen, halogen, lower alkyl, hydroxy, lower alkylthio, amino optionally substituted with lower alkyl, or lower alkoxy optionally substituted with a substituent selected from the group consisting of hydroxy, lower alkoxy, amino, lower alkylamino and aryl optionally substituted with lower alkoxy,
• R.sup.7 is hydrogen or lower alkyl,
• A is lower alkylene, and
• Q is O or N--R.sup.9, in which R.sup.9 is hydrogen or acyl,
• or its salt, which comprises;
• a) reacting a compound of the formula:
• ##STR13## wherein R.sup.4, R.sup.5, X.sup.1, X.sup.2, X.sup.3 and Q are each as defined above,
• or its salt with a compound of the formula:
• ##STR14## wherein X is a leaving group, and
• R.sup.1, R.sup.2, R.sup.3 and A are each as defined above,
• or its salt to give a compound of the formula:
• ##STR15## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, X.sup.1, X.sup.2, X.sup.3, Q and A are each as defined above,
• or its salt, or
• b) acylating a compound of the formula:
• ##STR16## wherein R.sup.10 is hydrogen or lower alkyl, and
• R.sup.1, R.sup.2, R.sup.4, R.sup.5, X.sup.1, X.sup.2, X.sup.3, Q and A are each as defined above,
• or its salt to give a compound of the formula:
• ##STR17## wherein R.sup.11 is acyl, and
• R.sup.1, R.sup.2, R.sup.4, R.sup.5, R.sup.10, X.sup.1, X.sup.2, X.sup.3, Q and A are each as defined above,
• or its salt, or
• c) acylating a compound of the formula:
• ##STR18## wherein R.sup.11 is acyl having amino, and
• R.sup.1, R.sup.2, R.sup.4, R.sup.5, R.sup.10, X.sup.1, X.sup.2, X.sup.3, Q and A are each as defined above,
• or its salt to give a compound of the formula:
• ##STR19## wherein R.sub.b.sup.11 is acyl having acylamino, and
• R.sup.1, R.sup.2, R.sup.4, R.sup.5, R.sup.10, X.sup.1, X.sup.2, X.sup.3, Q and A are each as defined above,
• or its salt, or
• d) reacting a compound of the formula:
• ##STR20## wherein (AA) is amino acid residue,
• Y is NH or lower alkenylene,
• Z is CH or N, and
• R.sup.1, R.sup.2, R.sup.4, R.sup.5, R.sup.10, X.sup.1, X.sup.2, X.sup.3, Q and A are each as defined above,
• or its reactive derivative at the carboxy group
• or a salt thereof with a compound of the formula:
• ##STR21## wherein R.sup.12 is hydrogen, lower alkyl, lower alkoxy(lower)alkyl, lower alkylamino(lower)alkyl, heterocyclic(lower)alkyl, a heterocyclic group, lower alkenyl, lower alkynyl, lower alkylcarbamoyloxy(lower)alkyl, lower alkoxycarbonyl(lower)alkyl, carboxy(lower)alkyl, lower alkylcarbamoyl(lower)alkyl, lower alkoxycarbonyl-ar(lower)alkyl, carboxy-ar(lower)alkyl, lower alkylcarbamoyl-ar(lower)alkyl, protected or unprotected hydroxy(lower)alkyl or aryl optionally substituted with lower alkylamino, and
• R.sup.13 is hydrogen, lower alkyl, lower alkoxy(lower)alkyl or protected or unprotected hydroxy(lower)alkyl, or
• R.sup.12 and R.sup.13 are taken together with the attached nitrogen atom to form a heterocyclic group optionally having suitable substituent(s),
• or its reactive derivative at the amino group
• or a salt thereof to give a compound of the formula:
• ##STR22## wherein R.sup.1, R.sup.2, R.sup.4, R.sup.5, R.sup.10, R.sup.12, R.sup.13, X.sup.1, X.sup.2, X.sup.3, A, (AA), Q, Y and Z are each as defined above,
• or its salt.