Biguanide derivative, a preparation method thereof and a pharmaceutical composition containing the biguanide derivative as an active ingredient

A compound of Formula 1 or a pharmaceutically acceptable salt thereof:

• wherein the compound of Formula 1 is N1-hexyl-N5-propyl biguanide;
• N1-hexyl-N5-cyclopropylmethyl biguanide;
• N1-hexyl-N5-cyclohexylmethyl biguanide;
• N1-hexyl-N5-benzyl biguanide;
• N1,N5-bis(4-chlorophenyl)biguanide;
• N1,N5-bis(3-chlorophenyl)biguanide;
• N1-(4-chloro)phenyl-N5-(4-methoxy)phenyl biguanide;
• N1,N5-bis(3-chloro-4-methoxyphenyl)biguanide;
• N1,N5-bis(3,4-dichlorophenyl)biguanide;
• N1,N5-bis(3,5-dichlorophenyl)biguanide;
• N1,N5-bis(4-bromophenyl)biguanide;
• N1-benzyl-N5-(pyridine-3-yl)methyl biguanide;
• N1-(phenethyl)-N5-propyl biguanide;
• N1-(phenethyl)-N5-cyclopropylmethyl biguanide;
• N1-(phenethyl)-N5-cycloheptyl biguanide;
• N1,N1-dimethyl-N5-methoxycarbonylethyl biguanide;
• N1,N1-dimethyl-N5-cycloheptyl biguanide;
• N1,N1-dimethyl-N5-cyclopropylmethyl biguanide;
• N1,N1-dimethyl-N5-(4-bromo)phenyl biguanide;
• N1,N1-dimethyl-N5-(furan-2-yl)methyl biguanide;
• N1,N1-dimethyl-N5-(pyridine-3-yl)methyl biguanide;
• N1,N1-diethyl-N5-(3-chloro)phenyl biguanide;
• N1,N1-dipropyl-N5-(3-chloro)phenyl biguanide;
• N1,N1-(ethyl)(propyl)-N5-(4-chloro)phenyl biguanide;
• N1,N1-dipropyl-N5-(isoquionline-5-yl)biguanide;
• N1,N1-dihexyl-N5-(3-chloro)phenyl biguanide;
• N1,N1,N5,N5-tetraethyl biguanide;
• N1,N1-diethyl-N5,N5-(cyclohexyl)(methyl)biguanide;
• N1,N1-dipropyl-N5,N5-diethyl biguanide;
• N1,N1-dipropyl-N5,N5-(methyl)(phenethyl)biguanide;
• or N1,N1-dipropyl-N5,N5-(4-hydroxylphenyl)(phenyl)biguanide.

A method of preparing a compound of Formula 1, comprising:

• reacting a compound of Formula 2 with dicyanoamide in at least one organic solvent to obtain a compound of Formula 3;
• and
• reacting the compound of Formula 3 with a compound of Formula 4 in at least one organic solvent to obtain the compound of Formula 1:
• wherein R1 is unsubstituted C1-7 alkyl;
• C1-4 alkyl substituted with C5-12 aryl;
• or C5-12 aryl,
• R2 is hydrogen;
• or unsubstituted C1-7 alkyl,
• R3 is hydrogen;
• or C5-12 aryl,
• R4 is a non-hydrogen substituent selected from the group consisting of unsubstituted C6-7 alkyl;
• C1-4 alkyl substituted with at least one non-hydrogen substituent selected from the group consisting of C5-12 heteroaryl and C1-4 alkoxycarbonyl;
• unsubstituted C5-7 cycloalkyl;
• C5-12 aryl;
• and C5-12 heteroaryl, and
• the aryl and heteroaryl may be unsubstituted or substituted with at least one non-hydrogen substituent selected from the group consisting of C1-4 alkoxy, hydroxyl and halogen, and the aryl and heteroaryl may be selected from the group consisting of phenyl, pyridinyl, furanyl and isoquinolinyl.