Novel calcium receptor active molecules and method for preparing same

A method for preparing the compounds of the following general formula I:

• 45
• in which:
• the group X represents a group —NR4, —CH═N— or —CHR5-NR4-,
• the group Y represents an oxygen or sulfur atom or a group NR, —CR5, —CHR5, —CR5=CR6- or —CHR5-CHR6-, on the condition that, when the group X represents the group —CH═N— or —CHR5-NR4-, the group Y represents an oxygen or sulfur atom or a group NR, —CR5 or —CHR5,
• the group R represents a hydrogen atom or an alkyl, aryl or aralkyl group,
• the groups R1, R5 and R6, which may be identical or different, each represent a hydrogen or halogen atom or an alkyl or alkoxy group,
• the group R2 represents a hydrogen atom or an alkyl group,
• the group R3 represents an aryl group,
• and the group R4 represents a hydrogen atom or an alkyl, aryl, aralkyl, alkylsulfonamide, arylsulfonamide or aralkylsulfonamide group,
• with the exception of the compounds for which
• X represents a group —CHR5-NR4,
• Y represents a group —CHR5,
• R5 represents a hydrogen atom,
• R4 represents a hydrogen atom or an alkyl or aralkyl group,
• R2 represents a hydrogen atom or an alkyl group,
• R3 represents an aryl group,
• R1 represents a hydrogen atom or an alkoxy group,
• and of the compounds of formulae:
• 46
• characterized in that it comprises the step of reduction of the amide of the following general formula V:
• 47
• in which:
• the group X represents a group —NR4, —CH═N— or —CHR5-NR4-,
• the group Y represents an oxygen or sulfur atom or a group NR, —CR5, —CHR5, —CR5=CR6- or —CHR5-CHR6-, on the condition that, when the group X represents the group —CH═N— or —CHR5-NR4-, the group Y represents an oxygen or sulfur atom or a group NR, —CR5 or —CHR5,
• the group R represents a hydrogen atom or an alkyl, aryl or aralkyl group,
• the groups R1, R5 and R6, which may be identical or different, each represent a hydrogen or halogen atom or an alkyl or alkoxy group,
• the group R2 represents a hydrogen atom or an alkyl group,
• the group R3 represents an aryl group,
• and the group R4 represents a hydrogen atom or an alkyl, aryl, aralkyl, alkylsulfonamide, arylsulfonamide or aralkylsulfonamide group,
• with the exception of the compounds for which
• X represents a group —CHR5-NR4,
• Y represents a group —CHR5,
• R5 represents a hydrogen atom,
• R4 represents a hydrogen atom or an alkyl or aralkyl group,
• R2 represents a hydrogen atom or an alkyl group,
• R3 represents an aryl group,
• R1 represents a hydrogen atom or an alkoxy group,
• and of the compounds of formula:
• 48

An amide of the following general formula V:

• 52
• in which:
• the group X represents a group —NR4, —CH═N— or —CHR5-NR4-,
• the group Y represents an oxygen or sulfur atom or a group NR, —CR5, —CHR5, —CR5=CR6- or —CHR5-CHR6-, on the condition that, when the group X represents the group —CH═N— or —CHR5-NR4-, the group Y represents an oxygen or sulfur atom or a group NR, —CR5 or —CHR5,
• the group R represents a hydrogen atom or an alkyl, aryl or aralkyl group,
• the groups R1, R5 and R6, which may be identical or different, each represent a hydrogen or halogen atom or an alkyl or alkoxy group,
• the group R2 represents a hydrogen atom or an alkyl group,
• the group R3 represents an aryl group,
• and the group R4 represents a hydrogen atom or an alkyl, aryl, aralkyl, alkylsulfonamide, arylsulfonamide or aralkylsultonamide group,
• and its salt with a pharmaceutically acceptable acid, in the form of a racemic mixture or of its optically pure isomer,
• with the exception of the compounds for which
• X represents a group —CHR5-NR4,
• Y represents a group —CHR5,
• R5 represents a hydrogen atom,
• R4 represents a hydrogen atom or an alkyl or aralkyl group,
• R2 represents a hydrogen atom or an alkyl group,
• R3 represents an aryl group,
• R1 represents a hydrogen atom or an alkoxy group,
• and of the compounds of formula:
• 53