The present application relates to a nitrogen-containing compound. The structural formula of the nitrogen-containing compound is as shown in a Formula 1, in which a ring A and a ring B are each independently selected from a benzene ring or a fused aromatic ring with 10 to 14 ring-forming carbon atoms, and at least one of the ring A and the ring B is selected from the fused aromatic ring with 10 to 14 ring-forming carbon atoms; L is selected from a single bond, a substituted or unsubstituted arylene group with 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group with 3 to 30 carbon atoms; and Het is a substituted or unsubstituted nitrogen-containing heteroaryl group with 3 to 30 carbon atoms. The nitrogen-containing compound of the present application can improve the luminous efficiency of an organic electroluminescent device and the conversion efficiency of a photoelectric conversion device using the nitrogen-containing compound. ##STR00001##

The present application relates to a nitrogen-containing compound. The structural formula of the nitrogen-containing compound is as shown in a Formula 1, in which a ring A and a ring B are each independently selected from a benzene ring or a fused aromatic ring with 10 to 14 ring-forming carbon atoms, and at least one of the ring A and the ring B is selected from the fused aromatic ring with 10 to 14 ring-forming carbon atoms; L is selected from a single bond, a substituted or unsubstituted arylene group with 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group with 3 to 30 carbon atoms; and Het is a substituted or unsubstituted nitrogen-containing heteroaryl group with 3 to 30 carbon atoms. The nitrogen-containing compound of the present application can improve the luminous efficiency of an organic electroluminescent device and the conversion efficiency of a photoelectric conversion device using the nitrogen-containing compound. ##STR00001##

The present invention relates to novel hydrazone derivatives in which a terminal amine group is substituted with an aryl group or a heteroaryl group, and uses thereof.

The present invention relates to novel hydrazone derivatives in which a terminal amine group is substituted with an aryl group or a heteroaryl group, and uses thereof.

A method for a high yield production of a difluoromethyl-substituted aromatic heterocyclic compound having a partial structure represented by formula (II), which includes reacting an N-oxido aromatic heterocyclic compound having a partial structure represented by formula (I) with tetrafluoroethylene in a solvent selected from an aromatic hydrocarbon solvent, an ester solvent, and an ether solvent.

##STR00001##

A method for a high yield production of a difluoromethyl-substituted aromatic heterocyclic compound having a partial structure represented by formula (II), which includes reacting an N-oxido aromatic heterocyclic compound having a partial structure represented by formula (I) with tetrafluoroethylene in a solvent selected from an aromatic hydrocarbon solvent, an ester solvent, and an ether solvent.

##STR00001##

A method for producing an aromatic heterocycle-substituted difluoroacetic acid derivative having a partial structure represented by the formula (III), by reacting an N-oxido aromatic heterocyclic compound having a partial structure represented by the formula (I) with tetrafluoroethylene in the presence of a compound represented by the formula (II): R—YH, in a solvent selected from an aromatic hydrocarbon solvent, an ester solvent and an ether solvent:

##STR00001##

A compound of formula (I) given below or a pharmaceutically acceptable salt of the compound is useful as an IDO/TDO inhibitor. Thus, the compound of formula (I) or the pharmaceutically acceptable salt of the compound can be used as, for example, a therapeutic agent for a disease or a disorder selected from tumor, infectious disease, neurodegenerative disorder, cataract, organ transplant rejection, autoimmune disease, postoperative cognitive impairment, and disease related to women's reproductive health [in the following formula (I), ring A represents an aromatic ring, a heterocyclic ring, or a condensed ring of two or more rings selected from an aromatic ring, and a heterocyclic ring, wherein ring A is selected from the group consisting of a benzene ring, a naphthalene ring, a quinoxaline ring, a thiophene ring, an indole ring, a benzothiophene ring, an imidazole ring, a quinoline ring, a quinazoline ring, and a pyridine ring; X, R.sup.1 and R.sup.2 represent a substituent on a ring atom constituting ring A, wherein R.sup.1 and R.sup.2 are bonded to adjacent ring atoms of ring A; m represents an integer of 1 or 2; X is a halogen atom, and when m is 2, each X is the same or different; R.sup.1 and R.sup.2 are the same or different; R.sup.1 and R.sup.2 independently represent a group represented from the following groups:

—(CH.sub.2).sub.n—Y—R.sup.4

wherein Y is selected from the group consisting of O, S, SO, SO.sub.2, and Se, n represents an integer of 1 to 8, R.sup.4 represents

##STR00001##

wherein R.sup.41, R.sup.42 and R.sup.47 are the same and are a hydrogen atom

##STR00002##

A compound of formula (I) given below or a pharmaceutically acceptable salt of the compound is useful as an IDO/TDO inhibitor. Thus, the compound of formula (I) or the pharmaceutically acceptable salt of the compound can be used as, for example, a therapeutic agent for a disease or a disorder selected from tumor, infectious disease, neurodegenerative disorder, cataract, organ transplant rejection, autoimmune disease, postoperative cognitive impairment, and disease related to women's reproductive health [in the following formula (I), ring A represents an aromatic ring, a heterocyclic ring, or a condensed ring of two or more rings selected from an aromatic ring, and a heterocyclic ring, wherein ring A is selected from the group consisting of a benzene ring, a naphthalene ring, a quinoxaline ring, a thiophene ring, an indole ring, a benzothiophene ring, an imidazole ring, a quinoline ring, a quinazoline ring, and a pyridine ring; X, R.sup.1 and R.sup.2 represent a substituent on a ring atom constituting ring A, wherein R.sup.1 and R.sup.2 are bonded to adjacent ring atoms of ring A; m represents an integer of 1 or 2; X is a halogen atom, and when m is 2, each X is the same or different; R.sup.1 and R.sup.2 are the same or different; R.sup.1 and R.sup.2 independently represent a group represented from the following groups:

—(CH.sub.2).sub.n—Y—R.sup.4

wherein Y is selected from the group consisting of O, S, SO, SO.sub.2, and Se, n represents an integer of 1 to 8, R.sup.4 represents

##STR00001##

wherein R.sup.41, R.sup.42 and R.sup.47 are the same and are a hydrogen atom

##STR00002##

A method of administering to a patient in need thereof or contacting with a biological sample, a compound related to Formula I-e ##STR00001##
or pharmaceutically acceptable compositions thereof, is useful to inhibit activity of TLR7/8 or a mutant thereof and/or to treat a TLR7/8-mediated disorder.