Novel 2-imino-1,3-thiazoline-based compounds and t-type calcium channel inhibitors containing the same

A method of preparing the compound represented by Chemical Formula I, comprising the steps of:

• heating/reflowing the compounds represented by Chemical Formulas II and III in a solution of a C1 to C5 alcohol for 5 to 20 hours at 20 to 130° C., to prepare the compound represented by Chemical Formula IV;
• adding a basic aqueous solution, heating/reflowing for 30 minutes to 5 hours at 20 to 120° C., and then adjusting the pH to 1 to 4 by adding a hydrogen halide, to prepare the compound represented by Chemical Formula V;
• and
• adding the compound represented by Chemical Formula VI and an amide condensation binder to the obtained compound represented by Chemical Formula V, and allowing them to react, to prepare the compound represented by Chemical Formula I:
• wherein
• R1 is a hydrogen atom, or a C1-C5 linear or branched alkyl group,
• R2, R3, and R4 are the same or different from one another, and are independently selected from the group consisting of a hydrogen atom, a halogen atom, a C1-C5 linear or branched alkyl group, a C1-C5 alkyloxy group, a trifluoromethyl group, a trifluoromethoxy group, a phenyloxy group, an amino group, a methanesulfoneamino group, a paratoluenesulfoneamino group, a nitro group, a C1-C5 cyanoalkyl group, a cyano group, a C1-C6 alkoxycarbonyl group, and a C3-C12 cycloalkyl group,
• R5 is selected from the group consisting of a C1-C5 linear or branched alkyl group, a C3-C6 cycloalkyl group, and a benzyl group,
• R6 is selected from the group consisting of a C3-C12 cycloalkyl group, a C4-C17 alkylcycloalkyl group, an adamantly group, a benzyl group, and a C8-C13 benzylalkyl group,
• n and m may be independently 0 or 1,
• X and Y are the same or different from each other and are independently selected from the group consisting of fluorine, chlorine, bromine, and iodine, and
• HX is present or absent.

A method of preparing the compound represented by Chemical Formula I comprising the step of heating/reflowing the compounds represented by Chemical Formulas VII and VIII in a solution of a C1 to C5 alcohol for 5 to 25 hours at 20 to 130° C., and allowing them to directly react, to prepare the compound represented by Chemical Formula I:

• wherein
• R1 is a hydrogen atom, or a C1-C5 linear or branched alkyl group,
• R2, R3, and R4 are the same or different from one another, and are independently selected from the group consisting of a hydrogen atom, a halogen atom, a C1-C5 linear or branched alkyl group, a C1-C5 alkyloxy group, a trifluoromethyl group, a trifluoromethoxy group, a phenyloxy group, an amino group, a methanesulfoneamino group, a paratoluenesulfoneamino group, a nitro group, a C1-C5 cyanoalkyl group, a cyano group, a C1-C6 alkoxycarbonyl group, and a C3-C12 cycloalkyl group,
• R5 is selected from the group consisting of a C1-C5 linear or branched alkyl group, a C3-C6 cycloalkyl group, and a benzyl group,
• R6 is selected from the group consisting of a C3-C12 cycloalkyl group, a C4-C17 alkylcycloalkyl group, an adamantly group, a benzyl group, and a C8-C13 benzylalkyl group,
• n and m are independently 0 or 1,
• HX is present or absent, and
• when HX is present, X is a halogen atom.