The present application provides a one-pot catalytic process which involves the formation of 1,4-dibenzodiazepines from o-haloaldimines (either pre-formed or formed in situ) of formula (I) and o-haloanilines of formula (II) via a palladium catalyzed Buchwald-Hartwig reaction and a cyclization sequence, to afford the 1,4-dibenzodiazepine products of formula (III). The present application describes the preparation of the 1,4-dibenzodiazepine products of formula (III) from simple commercial raw materials by efficient processes. ##STR00001##

Compounds represented by the following general formula (I), which has a P2X4 receptor antagonistic activity (in the formula, R.sup.1, R.sup.2 and R.sup.3 represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom, and the like, X represents C or N, Y represents N or C(O), provided that when X is C, Y represents N, and when X is N, Y represents C(O), the double line consisting of the solid line and the broken line represents a single bond or double bond, n represents an integer of 0 to 6, Z represents O, S, or an atomic bond, and A represents benzene ring, pyridine ring, and the like).

##STR00001##

Compounds represented by the following general formula (I), which has a P2X4 receptor antagonistic activity (in the formula, R.sup.1, R.sup.2 and R.sup.3 represent hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a halogen atom, and the like, X represents C or N, Y represents N or C(O), provided that when X is C, Y represents N, and when X is N, Y represents C(O), the double line consisting of the solid line and the broken line represents a single bond or double bond, n represents an integer of 0 to 6, Z represents O, S, or an atomic bond, and A represents benzene ring, pyridine ring, and the like).

##STR00001##

A heterocyclic compound represented by the general formula (1) or a salt thereof: ##STR00001## wherein m, l, and n respectively represent an integer of 1 or 2; X represents O or CH.sub.2; R.sup.1 represents hydrogen, a lower alkyl group, a hydroxy-lower alkyl group, a protecting group, or a tri-lower alkylsilyloxy-lower alkyl group; R.sup.2 and R.sup.3, which are the same or different, each independently represent hydrogen or a lower alkyl group; or R.sub.2 and R.sub.3 are bonded to form a cyclo-C3-C8 alkyl group; and R.sup.4 represents an aromatic group or a heterocyclic group, wherein the aromatic or heterocyclic group may have one or more arbitrary substituent(s).

The present invention relates to a diazepine derivative represented by the following general formula (I) (in the formula, R.sup.1 and R.sup.2 represent hydrogen atom and the like, or R.sup.1 and R.sup.2 bind together to form a naphthalene ring and the like together with the benzene ring to which they bind, R.sup.3 and R.sup.4 represent hydrogen atom and the like, R.sup.5 represents hydrogen atom and the like, R.sup.6 and R.sup.7 represent hydrogen atom and the like, X represents C, CH or N, Y represents N, NH or C(?O), provided that when X is N, Y is not N or NH, and when X is C or CH, Y is not C(?O), Z represents oxygen atom or sulfur atom, A represents benzene ring and the like, B represents NHC(?O) and the like, D represents an atomic bond and the like, E represents an atomic bond and the like, G represents benzene which may be substituted and the like, and m represents an integer of 0 to 5) or a pharmacologically acceptable salt thereof, and a P2X4 receptor antagonist. ##STR00001##

The present invention relates to a diazepine derivative represented by the following general formula (I) (in the formula, R.sup.1 and R.sup.2 represent hydrogen atom and the like, or R.sup.1 and R.sup.2 bind together to form a naphthalene ring and the like together with the benzene ring to which they bind, R.sup.3 and R.sup.4 represent hydrogen atom and the like, R.sup.5 represents hydrogen atom and the like, R.sup.6 and R.sup.7 represent hydrogen atom and the like, X represents C, CH or N, Y represents N, NH or C(?O), provided that when X is N, Y is not N or NH, and when X is C or CH, Y is not C(?O), Z represents oxygen atom or sulfur atom, A represents benzene ring and the like, B represents NHC(?O) and the like, D represents an atomic bond and the like, E represents an atomic bond and the like, G represents benzene which may be substituted and the like, and m represents an integer of 0 to 5) or a pharmacologically acceptable salt thereof, and a P2X4 receptor antagonist. ##STR00001##

The present invention relates to a diazepine derivative represented by the following general formula (I) (in the formula, R.sup.1 and R.sup.2 represent hydrogen atom and the like, or R.sup.1 and R.sup.2 bind together to form a naphthalene ring and the like together with the benzene ring to which they bind, R.sup.3 and R.sup.4 represent hydrogen atom and the like, R.sup.5 represents hydrogen atom and the like, R.sup.6 and R.sup.7 represent hydrogen atom and the like, X represents C, CH or N, Y represents N, NH or C(O), provided that when X is N, Y is not N or NH, and when X is C or CH, Y is not C(O), Z represents oxygen atom or sulfur atom, A represents benzene ring and the like, B represents NHC(O) and the like, D represents an atomic bond and the like, E represents an atomic bond and the like, G represents benzene which may be substituted and the like, and m represents an integer of 0 to 5) or a pharmacologically acceptable salt thereof, and a P2X4 receptor antagonist.

##STR00001##

The present invention relates to a diazepine derivative represented by the following general formula (I) (in the formula, R.sup.1 and R.sup.2 represent hydrogen atom and the like, or R.sup.1 and R.sup.2 bind together to form a naphthalene ring and the like together with the benzene ring to which they bind, R.sup.3 and R.sup.4 represent hydrogen atom and the like, R.sup.5 represents hydrogen atom and the like, R.sup.6 and R.sup.7 represent hydrogen atom and the like, X represents C, CH or N, Y represents N, NH or C(O), provided that when X is N, Y is not N or NH, and when X is C or CH, Y is not C(O), Z represents oxygen atom or sulfur atom, A represents benzene ring and the like, B represents NHC(O) and the like, D represents an atomic bond and the like, E represents an atomic bond and the like, G represents benzene which may be substituted and the like, and m represents an integer of 0 to 5) or a pharmacologically acceptable salt thereof, and a P2X4 receptor antagonist.

##STR00001##

The present invention relates to a diazepine derivative represented by the following general formula (I) (in the formula, R.sup.1 and R.sup.2 represent hydrogen atom and the like, or R.sup.1 and R.sup.2 bind together to form a naphthalene ring and the like together with the benzene ring to which they bind, R.sup.3 and R.sup.4 represent hydrogen atom and the like, R.sup.5 represents hydrogen atom and the like, R.sup.6 and R.sup.7 represent hydrogen atom and the like, X represents C, CH or N, Y represents N, NH or C(?O), provided that when X is N, Y is not N or NH, and when X is C or CH, Y is not C(?O), Z represents oxygen atom or sulfur atom, A represents benzene ring and the like, B represents NHC(?O) and the like, D represents an atomic bond and the like, E represents an atomic bond and the like, G represents benzene which may be substituted and the like, and m represents an integer of 0 to 5) or a pharmacologically acceptable salt thereof, and a P2X4 receptor antagonist. ##STR00001##

The present invention relates to a diazepine derivative represented by the following general formula (I) (in the formula, R.sup.1 and R.sup.2 represent hydrogen atom and the like, or R.sup.1 and R.sup.2 bind together to form a naphthalene ring and the like together with the benzene ring to which they bind, R.sup.3 and R.sup.4 represent hydrogen atom and the like, R.sup.5 represents hydrogen atom and the like, R.sup.6 and R.sup.7 represent hydrogen atom and the like, X represents C, CH or N, Y represents N, NH or C(?O), provided that when X is N, Y is not N or NH, and when X is C or CH, Y is not C(?O), Z represents oxygen atom or sulfur atom, A represents benzene ring and the like, B represents NHC(?O) and the like, D represents an atomic bond and the like, E represents an atomic bond and the like, G represents benzene which may be substituted and the like, and m represents an integer of 0 to 5) or a pharmacologically acceptable salt thereof, and a P2X4 receptor antagonist. ##STR00001##