The present disclosure relates to novel synthetic method of making 1, 4-diazo N-heterocycles via intermolecular amphoteric diamination of allenes, and to the compounds made by the novel synthetic method.

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).

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 disclosure relates to substituted phenyl sulfonyl phenyl triazole thiones, pharmaceutical compositions containing them, and methods of using them.

The present disclosure relates to substituted phenyl sulfonyl phenyl triazole thiones, pharmaceutical compositions containing them, and methods of using them.

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).