Disclosed are processes and intermediates for the preparation of compound (X), which is currently being investigated for the treatment of prostate cancer. ##STR00001##

Disclosed are processes and intermediates for the preparation of compound (X), which is currently being investigated for the treatment of prostate cancer. ##STR00001##

A compound (A) is represented by the formula (1): ##STR00001## wherein R.sup.1 is a hydrogen atom or an alkali metal atom, R.sup.2 is a hydrogen atom or an alkali metal atom, R.sup.3 is a hydrogen atom or a methyl group, Z is a divalent or trivalent organic group, and the lines consisting of a solid line and a broken line bonded to Z represent a single bond or a double bond.

A compound (A) is represented by the formula (1): ##STR00001## wherein R.sup.1 is a hydrogen atom or an alkali metal atom, R.sup.2 is a hydrogen atom or an alkali metal atom, R.sup.3 is a hydrogen atom or a methyl group, Z is a divalent or trivalent organic group, and the lines consisting of a solid line and a broken line bonded to Z represent a single bond or a double bond.

The disclosure relates to a compound, having a structure of Formula I or a pharmaceutically acceptable salt thereof, herein, R1 is selected from hydrogen, fluorine, and chlorine; R2 and R3 are independently selected from hydrogen, alkyl, a substituted alkyl, alkenyl or a substituted alkenyl, alkynyl or a substituted alkynyl, and aryl, or R2 and R3 are connected to form a ring selected from a cycloalkyl, a substituted cycloalkyl, an aromatic heterocycle or a non-aromatic heterocycle; R4 is selected from hydrogen, cyano, alkyl, a substituted alkyl, alkenyl or a substituted alkenyl, alkynyl or a substituted alkynyl, and aryl; and R5 is selected from hydrogen, halogen, and haloalkyl. The disclosure further relates to a pharmaceutical composition containing the compound. The compound and the composition of the disclosure show significant activity in an aspect of treating AR-prostate cancer and triple-negative breast cancer.

The disclosure relates to a compound, having a structure of Formula I or a pharmaceutically acceptable salt thereof, herein, R1 is selected from hydrogen, fluorine, and chlorine; R2 and R3 are independently selected from hydrogen, alkyl, a substituted alkyl, alkenyl or a substituted alkenyl, alkynyl or a substituted alkynyl, and aryl, or R2 and R3 are connected to form a ring selected from a cycloalkyl, a substituted cycloalkyl, an aromatic heterocycle or a non-aromatic heterocycle; R4 is selected from hydrogen, cyano, alkyl, a substituted alkyl, alkenyl or a substituted alkenyl, alkynyl or a substituted alkynyl, and aryl; and R5 is selected from hydrogen, halogen, and haloalkyl. The disclosure further relates to a pharmaceutical composition containing the compound. The compound and the composition of the disclosure show significant activity in an aspect of treating AR-prostate cancer and triple-negative breast cancer.

A novel method for synthesizing deuterated amides and deuterated sulfonamides includes the following steps: (1) adding a compound M, DMAP, R.sup.3—X to a solvent to obtain a compound N after a reaction is complete; and (2) adding the compound N, R.sup.4—NH—R.sup.5, or a salt and base thereof to a solvent, and purifying after a reaction is complete to obtain a compound I.

##STR00001##

The present disclosure provides methods for producing N-(fluorosulfonyl)azoles, sulfonyldiazoles, or related derivatives thereof, and the related products including N-(fluorosulfonyl)azoles, sulfonyldiazoles, and related derivatives thereof. For example, an N-(fluorosulfonyl)azole is obtained by reaction of sulfuryl fluoride with an azoles, an azolate salt, an N-silylazole, or a combination thereof. Symmetric and asymmetric sulfonyldiazoles are obtained by further reaction of such an N-(fluorosulfonyl)azole with azoles, azolate salts, or N-silylazoles. A sulfonyldiazole can be also produced by reacting sulfuryl fluoride with an azole, an N-silylazole, or a combination thereof in one pot.

The present disclosure provides methods for producing N-(fluorosulfonyl)azoles, sulfonyldiazoles, or related derivatives thereof, and the related products including N-(fluorosulfonyl)azoles, sulfonyldiazoles, and related derivatives thereof. For example, an N-(fluorosulfonyl)azole is obtained by reaction of sulfuryl fluoride with an azoles, an azolate salt, an N-silylazole, or a combination thereof. Symmetric and asymmetric sulfonyldiazoles are obtained by further reaction of such an N-(fluorosulfonyl)azole with azoles, azolate salts, or N-silylazoles. A sulfonyldiazole can be also produced by reacting sulfuryl fluoride with an azole, an N-silylazole, or a combination thereof in one pot.

Provided herein are dUTPase inhibitors, compositions comprising such compounds and methods of using such compounds and compositions.