Derivatives of dioxane-2-alkyl carbamates, preparation thereof and application thereof in therapeutics

A method for preparing a compound of formula (I),

• in which
• R1 represents a phenyl or naphthalenyl group optionally substituted with one or more halogen atoms or hydroxyl, cyano, nitro, (C1–C3)alkyl, trifluoromethyl, trifluoromethoxy, benzyloxy, (C3–C6)cycloalkyl-O— or (C3–C6)cycloalkyl(C1–C3)alkoxy groups;
• R2 represents a group of general formula CHR3CONHR4 or a (C1–C3)alkyl, (C3–C5)cycloalkyl or (pyridin-4-yl)methyl group;
• and
• wherein
• R3 represents a hydrogen atom or a methyl group;
• R4 represents a hydrogen atom or a (C1–C3)alkyl, (C3–C5)cycloalkyl or (pyridin-4-yl)methyl group;
• n represents a number ranging from 1 to 3;
• comprising the step consisting in converting the carbamate ester of general formula (Ia)
• in which R1, R3 and n are as defined above and R5 represents a methyl or ethyl group, to a compound of general formula (I), either by direct aminolysis by means of an amine of general formula R4NH2 in which R4 is as defined above, or by hydrolysis to an acid of general formula (Ia), in which R5 represents a hydrogen atom, followed by coupling with an amine of general formula R4NH2 in which R4 is as defined above.

A method for preparing a compound of formula (I),

• in which
• R1 represents a phenyl or naphthalenyl group optionally substituted with one or more halogen atoms or hydroxyl, cyano, nitro, (C1–C3)alkyl, (C1–C3)alkoxy, trifluoromethyl, trifluoromethoxy, benzyloxy, (C3–C6)cycloalkyl-O— or (C3–C6)cycloalkyl(C1–C3)alkoxy groups;
• R2 represents a group of general formula CHR3CONHR4 in which R3 represents a hydrogen atom or a methyl group and R4 represents a hydrogen atom or a (C1–C3)alkyl, (C3–C5)cycloalkyl or (pyridin-4-yl)methyl group;
• and
• n represents a number ranging from 1 to 3;
• comprising the step consisting in converting the oxazolidinedione derivative of general formula (VI)
• in which R1, R3 and n are as defined above, to a compound of general formula (I) by aminolysis by means of an amine of general formula R4NH2 where R4 is as defined above.

A compound corresponding to general formula (Ia)

• in which
• R1 represents a phenyl or a naphthalenyl group optionally substituted with one or more halogen atoms or hydroxyl, cyano, nitro, (C1–C3)alkyl, (C1–C3)alkoxy, trifluoromethyl, trifluoromethoxy, benzyloxy or (C3–C6)cycloalkyl(C1–C3)alkoxy groups;
• R3 represents a hydrogen atom or a methyl group;
• R5 represents a hydrogen atom, or a methyl or ethyl group;
• and
• n represents a number ranging from 1 to 3.

A compound corresponding to general formula (VI)

• in which
• R1 represents a phenyl or naphthalenyl group optionally substituted with one or more halogen atoms or hydroxyl, cyano, nitro, (C1–C3)alkyl, (C1–C3)alkoxy, trifluoromethyl, trifluoromethoxy, benzyloxy or (C3–C6)cycloalkyl(C1–C3)alkoxy groups;
• R3 represents a hydrogen atom or a methyl group;
• and
• n represents a number ranging from 1 to 3.