Pyrrole derivative or pharmaceutically or sitologically acceptable salts thereof, and composition for prevention, amelioration or treatment of gastrointestinal disorders comprising same as active ingredient

A method for producing a pyrrole derivative comprising the steps of:

• (1) reacting a compound of the following formula 2 and a sulfonyl compound (R1SO2Cl) in the presence of an organic solvent and a base to prepare a compound of the following formula 3;
• and
• (2) reacting the compound of the following formula 3 and deuterated methylamine (methyl-d3-amine) in the presence of an organic solvent and a reducing agent to prepare a compound of the following formula 4:
• wherein,
• R1 is hydrogen, phenyl, quinolinyl, pyridinyl, pyrimidinyl, piperidinyl, thienyl or imidazolyl, and wherein R1 except hydrogen is unsubstituted or substituted with 1 to 5 substituents independently selected from the group consisting of C1-C6 alkyl, C1-C6 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, cyano, nitro, phenyl and halophenyl,
• R2, R3 and R4 are each independently hydrogen or fluoro, provided that R2, R3 and R4 are not hydrogen at the same time,
• R5 is hydrogen or chloro, and
• X is carbon or nitrogen.

A method for producing the pyrrole derivative of formula 13, comprising the steps:

• (1) reacting the compound of the following formula 9 and a sulfonyl compound (R1SO2Cl) in the presence of a chloroform organic solvent and a base to prepare a compound of the following formula 10;
• (2) reacting the compound of the following formula 10 and a reducing agent in the presence of an organic solvent to prepare a compound of the following formula 11;
• (3) reacting the compound of the following formula 11 in the presence of an oxidizing agent to prepare a compound of the following formula 12;
• and
• (4) reacting the compound of the following formula 12 and deuterated methylamine (methyl-d3-amine) in the presence of an organic solvent and a reducing agent to prepare a compound of the following formula 13:
• wherein,
• R1 is hydrogen, phenyl, quinolinyl, pyridinyl, pyrimidinyl, piperidinyl, thienyl or imidazolyl, and wherein R1 except hydrogen is unsubstituted or substituted with 1 to 5 substituents independently selected from the group consisting of C1-C6 alkyl, C1-C6 alkoxy, C1-C4 haloalkyl, C1-C4 haloalkoxy, halogen, cyano, nitro, phenyl and halophenyl, and
• R2, R3 and R4 are each independently hydrogen or fluoro, provided that R2, R3 and R4 are not hydrogen at the same time.