The present invention provides an industrially advantageous production method of (1R,2S)-2-{[((2,4-dimethylpyrimidin-5-yl)oxy}methyl]-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropane-1-carboxamide. (1R,2S)-2-{[((2,4-Dimethylpyrimidin-5-yl)oxy}methyl]-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropane-1-carboxamide (compound [A]) is produced by an industrially advantageous method by a route via a novel compound. ##STR00001##
wherein each symbol is as described in the description.

The present invention provides an industrially advantageous production method of (1R,2S)-2-{[((2,4-dimethylpyrimidin-5-yl)oxy}methyl]-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropane-1-carboxamide. (1R,2S)-2-{[((2,4-Dimethylpyrimidin-5-yl)oxy}methyl]-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropane-1-carboxamide (compound [A]) is produced by an industrially advantageous method by a route via a novel compound. ##STR00001##
wherein each symbol is as described in the description.

The present invention provides arylalkylamine compounds as calcium sensing receptor modulators (CaSR). In particular, the compounds described herein are useful for treating, managing, and/or lessening the severity of diseases, disorders, syndromes and/or conditions associated with the modulation of calcium sensing receptors (CaSR). The invention also provides herein the pharmaceutical compositions thereof, and methods for treating, managing, and/or lessening the severity of diseases, disorders, syndromes and/or conditions associated with the modulation of CaSR. The invention also relates to process for the preparation of the compounds of the invention. (Formula I)

##STR00001##

The present invention provides arylalkylamine compounds as calcium sensing receptor modulators (CaSR). In particular, the compounds described herein are useful for treating, managing, and/or lessening the severity of diseases, disorders, syndromes and/or conditions associated with the modulation of calcium sensing receptors (CaSR). The invention also provides herein the pharmaceutical compositions thereof, and methods for treating, managing, and/or lessening the severity of diseases, disorders, syndromes and/or conditions associated with the modulation of CaSR. The invention also relates to process for the preparation of the compounds of the invention. (Formula I) ##STR00001##

The present invention provides arylalkylamine compounds as calcium sensing receptor modulators (CaSR). In particular, the compounds described herein are useful for treating, managing, and/or lessening the severity of diseases, disorders, syndromes and/or conditions associated with the modulation of calcium sensing receptors (CaSR). The invention also provides herein the pharmaceutical compositions thereof, and methods for treating, managing, and/or lessening the severity of diseases, disorders, syndromes and/or conditions associated with the modulation of CaSR. The invention also relates to process for the preparation of the compounds of the invention. (Formula I) ##STR00001##

Provided is a fluorene compound having a sulfonic acid ester structure and an allyl group, the compound being represented by formula (1).

##STR00001##

(In the formula, R.sup.1 each independently are a hydrogen atom or a methyl group. R.sup.2 each independently are a C1-20 hydrocarbyl group, some or all of the hydrogen atoms of which may be substituted by a halogen atom, a nitro group, or a cyano group, and an ester bond or an ether bond may be present between the carbon-carbon bonds thereof.)

Provided is a fluorene compound having a sulfonic acid ester structure and an allyl group, the compound being represented by formula (1).

##STR00001##

(In the formula, R.sup.1 each independently are a hydrogen atom or a methyl group. R.sup.2 each independently are a C1-20 hydrocarbyl group, some or all of the hydrogen atoms of which may be substituted by a halogen atom, a nitro group, or a cyano group, and an ester bond or an ether bond may be present between the carbon-carbon bonds thereof.)

Provided is a method of preparing a benzenesulfonyl compound by reacting a compound represented by the following Chemical Formula,

##STR00001##

and an n-hydric alcohol in the presence of a phase transfer catalyst and an alkali metal hydroxide, wherein R.sup.1 to R.sup.5 are independently of one another hydrogen, a halogen, C1-C7 alkoxy, or C1-C7 alkyl; X is a residue derived from the n-hydric alcohol; n is an integer of 1 to 4; and Y is a halogen. The method has an excellent reaction speed even under mild reaction conditions and may produce the benzenesulfonyl compound in a high yield.

Provided is a method of preparing a benzenesulfonyl compound by reacting a compound represented by the following Chemical Formula,

##STR00001##

and an n-hydric alcohol in the presence of a phase transfer catalyst and an alkali metal hydroxide, wherein R.sup.1 to R.sup.5 are independently of one another hydrogen, a halogen, C1-C7 alkoxy, or C1-C7 alkyl; X is a residue derived from the n-hydric alcohol; n is an integer of 1 to 4; and Y is a halogen. The method has an excellent reaction speed even under mild reaction conditions and may produce the benzenesulfonyl compound in a high yield.