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 compound according to following formula can be prepared,

##STR00001##

where R1 is an F or I residue.

A compound according to following formula can be prepared,

##STR00001##

where R1 is an F or I residue.

A high yielding extraction process for the purification of N-(2,4-dichloro-5-(4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)methanesulfonamide (sulfentrazone) by selectively partitioning the desired product from the crude mixture, thereby increasing its purity by decreasing the presence of unwanted impurities and improving the color and particle size distribution of the final sulfentrazone product. The selective partitioning is achieved by the sequential use of an organic solvent, water, aqueous inorganic base and a concentrated aqueous inorganic acid.

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, an aliphatic ring, a heterocyclic ring, or a condensed ring of two or more rings selected from an aromatic ring, an aliphatic ring and a heterocyclic ring; X, R.sup.1 and R.sup.2 represent a substituent on a ring atom constituting ring A; m represents an integer of 0 to 6; X represents, for example, a halogen atom; and R.sup.1 and R.sup.2 are the same or different and are selected from, for example, the group consisting of groups of formula (a) or formula (b); and in the following formula (a) and formula (b), Y is selected from the group consisting of O, S, and Se, Z is selected from the group consisting of O, S, and Se, n represents an integer of 1 to 8, r represents an integer of 1 to 8, s represents an integer of 1 to 8, R.sup.4 represents, for example, C(NH)HN.sub.2, and R.sup.6 represents, for example, a substituted or unsubstituted aryl group].

##STR00001##

Disclosed herein are compounds of formula I:

##STR00001##

or a salt thereof and compositions comprising a compound of formula I or a pharmaceutically acceptable salt thereof. Also disclosed herein are methods for treating or preventing a bacterial infection in an animal comprising administering to the animal a compound of formula I or a pharmaceutically acceptable salt thereof, alone or in combination with a bacterial efflux pump inhibitor.

Disclosed herein are compounds of formula I:

##STR00001##

or a salt thereof and compositions comprising a compound of formula I or a pharmaceutically acceptable salt thereof. Also disclosed herein are methods for treating or preventing a bacterial infection in an animal comprising administering to the animal a compound of formula I or a pharmaceutically acceptable salt thereof, alone or in combination with a bacterial efflux pump inhibitor.

Provided herein is novel N-heterocyclic ketones that are useful for treatment of hypertrophic cardiomyopathy (HCM) and other heart diseases. The preparation method thereof, pharmaceutical compositions comprising the compound.

Provided herein is novel N-heterocyclic ketones that are useful for treatment of hypertrophic cardiomyopathy (HCM) and other heart diseases. The preparation method thereof, pharmaceutical compositions comprising the compound.