Novel pyrrole derivative compound and pharmaceutical composition for inhibiting gastric acid secretion comprising same

Abstract

The present invention relates to a novel pyrrole derivative compound or a pharmaceutically acceptable salt thereof. In addition, the present invention relates to a pharmaceutical composition for potassium-competitive inhibition of gastric acid secretion and a pharmaceutical composition for preventing or treating diseases caused by gastric acid secretion disorder, the pharmaceutical composition containing the novel pyrrole derivative compound or a pharmaceutically acceptable salt thereof as an active component. The pyrrole derivative compound or the like according to the present invention is a potassium-competitive acid blocker (PCAB) and has an excellent H+ / K+ adenosine triphosphatase (ATPase) (proton pump) inhibition effect, and is thus widely used as a therapeutic agent for diseases caused by gastric acid secretion disorder.

Description

Novel pyrrole derivative compounds and pharmaceutical compositions for inhibiting gastric acid secretion containing the same The present invention relates to novel pyrrole derivative compounds or pharmaceutically acceptable salts thereof. In addition, the present invention relates to a pharmaceutical composition for inhibiting potassium-competitive gastric acid secretion comprising a novel pyrrole derivative compound or a pharmaceutically acceptable salt thereof as an active ingredient. In addition, the present invention relates to a pharmaceutical composition for the prevention or treatment of diseases caused by gastric acid secretion disorders, comprising a novel pyrrole derivative compound or a pharmaceutically acceptable salt thereof as an active ingredient. Although stomach acid plays positive roles such as protein digestion, absorption of minerals like calcium and iron, and sterilization of harmful microorganisms in ingested food, it is a highly acidic substance with a pH of approximately 1 to 2. Therefore, excessive secretion of stomach acid or reflux into the esophagus can lead to gastric ulcers or gastroesophageal reflux disease (GERD), including erosive reflux disease (ERD) and non-erosive reflux disease (NERD). Gastroesophageal reflux disease (GERD) is a condition in which stomach acid or contents reflux into the esophagus, causing a burning pain or heartburn in the chest. Normally, the esophageal sphincter between the esophagus and the stomach prevents stomach contents from refluxing; however, if the sphincter weakens or opens improperly, gastroesophageal reflux occurs. Increased reflux causes stomach acid and stomach contents to irritate the esophageal mucosa, leading to esophagitis, esophageal ulcers, and strictures. Symptoms of gastroesophageal reflux disease include heartburn, acid reflux, chronic cough, dysphagia, and chest pain. Gastric acid secretion occurs when parietal cells are activated by parietal stimulating factors, causing the secretory canaliculus to widen, and H + / K + This is accomplished by a mechanism in which adenosine triphosphatase (ATPase) (proton pump) is positioned on the cell membrane of parietal cells to exchange potassium ions from the gastric lumen with those in the cytoplasm. In other words, in response to various gastric acid secretion stimulating factors, the proton pump consumes ATP and expels hydrogen ions into the gastric lumen by exchanging hydrogen ions in the cytoplasm with potassium ions in the gastric lumen. H2-receptor antagonists (H2RAs) and proton pump inhibitors (PPIs) have been the primary drugs used to inhibit gastric acid secretion. However, H2RAs do not directly inhibit the proton pump but rather block only the histamine pathway within the gastric acid secretion system, resulting in only partial effects and a limitation in that tolerance develops easily. Additionally, PPIs also exhibited limitations because they exert their effects after undergoing an activation process as prodrugs; consequently, they have a slow onset of action and a short half-life, leading to limited inhibition of nocturnal acid breakthrough (NAB). Other limitations included drug interactions related to metabolic pathways and restrictions on drug administration timing due to dietary influences. Meanwhile, potassium-competitive acid blockers (PCABs) inhibit gastric acid secretion by competitively binding to proton pumps and suppressing their action. PCABs are recommended for the initial treatment of gastroesophageal reflux disease due to their efficacy comparable to that of proton pump inhibitors. Among the PCAB drugs currently marketed in Korea, tegoprazan is used for the treatment of erosive and non-erosive gastroesophageal reflux disease, and as part of antibiotic combination therapy for Helicobacter pylori eradication in patients with gastric ulcers, peptic ulcers, and / or chronic atrophic gastritis. Structurally, tegoprazan has a benzimidazole carboxamide structure similar to existing PPIs, which are sulfinyl benzimidazole derivatives. On the other hand, vonoprazan is a sulfonyl pyrrole, which differs structurally from tegoprazan; therefore, although they belong to the same drug class, there is no class effect between them. Tegoprazan has been confirmed to inhibit nocturnal gastric acid hypersecretion, and since it does not inhibit major hepatic metabolic enzymes, the risk of drug interactions is not significant. Fexuprazan is the 34th domestic new drug to receive approval from the Ministry of Food and Drug Safety for the treatment of erosive gastroesophageal reflux disease and become eligible for reimbursement. H in parietal cells + / K + ATPase's K + Reversible channel, K + It inhibits gastric acid secretion by competitively blocking it. Potassium-competitive acid blockers (PCABs) act directly without an activation process, and H + / K + ATPase's K + Reversible channel, K + It has the advantages of competitively blocking, acting on both inactive and active proton pumps, being stable in the gastric tubules, having a long half-life, and being able to be taken regardless of meals. After diligent research, the inventors have found that peptic ulcers, stomach . Duodenal ulcer, gastritis, stomach .We prepared pyrrole derivative compounds of a novel structure that can be usefully employed in the prevention or treatment of gastrointestinal inflammatory diseases or acid-related diseases, such as esophageal reflux disease (GERD) and non-erosive reflux disease (NERD), and confirmed that the novel pyrrole derivative compounds exhibit excellent proton pump inhibitory activity, thereby completing the present invention. The object of the present invention is to provide a novel pyrrole derivative compound or a pharmaceutically acceptable salt thereof. Another object of the present invention is to provide a pharmaceutical composition for inhibiting potassium-competitive gastric acid secretion comprising a novel pyrrole derivative compound or a pharmaceutically acceptable salt thereof as an active ingredient. Another object of the present invention is to provide a pharmaceutical composition for the prevention or treatment of diseases caused by gastric acid secretion disorders, comprising a novel pyrrole derivative compound or a pharmaceutically acceptable salt thereof as an active ingredient. The present invention provides a compound represented by the following chemical formula I or a pharmaceutically acceptable salt: [Chemical Formula I] In chemical formula I, is a heterobicyclic ring, and R1 is a phenyl, or a 5- or 6-membered hetero ring, and R2 is H, or a C1-C3 alkoxy, and R3 is H, or C1-C4 alkyl, and R4 is H, or C1-C4 alkyl. In chemical formula I, Is , , , , , , , , , , , , , , , , , , , , , , and It may be selected from a group consisting of In chemical formula I, R1 is , , , , , , , , , , , , , , , , , , , , , , , and It may be selected from a group consisting of In chemical formula I, R2 and R3 can each independently be H, and R4 can be methyl. The compound represented by Formula I of the present invention or its pharmaceutically acceptable salt is, for example, as follows: 1-(1-(benzofuran-5-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(5-methylthiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(4-methylthiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(2-methylthiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-4-(2,5-dimethylthiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 4-(1-(benzofuran-5-yl-sulfonyl)-4-((methylamino)methyl)-1H-pyrrole-2-yl)thiophene-2-carbonitrile trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(2-chlorothiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(isothiazole-4-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(furan-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(2,5-dimethylfuran-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(1H-pyrazole-4-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(1-methyl-1H-pyrazole-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; Ethyl 2-(4-(1-(benzofuran-5-yl-sulfonyl)-4-((methylamino)methyl)-1H-pyrrole-2-yl)-1H-pyrazole-1-yl)acetate trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(furan-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(thiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(4-(1-(benzofuran-5-yl-sulfonyl)-4-((methylamino)methyl)-1H-pyrrole-2-yl)thiophene-2-yl)ethane-1-one trifluoroacetate; 4-(1-(benzofuran-5-yl-sulfonyl)-4-((methylamino)methyl)-1H-pyrrole-2-yl)thiophene-2-carboxamide trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(5-fluorothiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(3-methylthiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(5-methylthiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(4-methylthiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-7-yl-sulfonyl)-5-(thiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; N-methyl-1-(1-(thieno[3,2-b]pyridine-6-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)methaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(thiazole-5-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-6-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(5-(trifluoromethyl)thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzo[b]thiophene-6-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzo[d]thiazole-6-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-((2,2-difluorobenzo[d][1,3]dioxol-4-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 6-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]thiazole-2(3H)-one trifluoroacetate; 3-methyl-6-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]thiazole-2(3H)-one trifluoroacetate; 6-((2-(isothiazole-4-yl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]thiazole-2(3H)-one trifluoroacetate; 3-methyl-5-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate; 1-(1-((2,3-dihydrobenzofuran-5-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 3,3-dimethyl-5-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)indolin-2-one trifluoroacetate; 1,3-dimethyl-5-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)-1,3-dihydro-2H-benzo[d]imidazole-2-one trifluoroacetate; 6-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]thiazole-2(3H)-one trifluoroacetate; 6-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate; 1-(1-(benzo[d][1,3]dioxol-5-ylsulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(indolin-5-ylsulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-((2,3-dihydro-1H-indene-5-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 6-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)-2H-benzo[b][1,4]oxazine-3(4H)-one trifluoroacetate; 6-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)-2H-benzo[b][1,4]oxazine-3(4H)-one trifluoroacetate; 6-((2-(2,4-difluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)-2H-benzo[b][1,4]oxazine-3(4H)-one trifluoroacetate; 7-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)-2H-benzo[b][1,4]oxazine-3(4H)-one trifluoroacetate; 1-(1-((3,4-dihydro-2H-benzo[b][1,4]oxazine-6-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; N-methyl-1-(1-((2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine-7-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)methaneamine trifluoroacetate; 1-(1-((3,4-dihydro-2H-benzo[b][1,4]oxazine-7-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; N-methyl-1-(1-((2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine-8-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)methaneamine trifluoroacetate; 5-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate; and 5-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate. Preferred examples of the compound of Formula 1 of the present invention or pharmaceutically acceptable salts thereof include the following: 1-(1-(benzofuran-5-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(5-methylthiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(4-methylthiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(2-methylthiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-4-(2,5-dimethylthiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 4-(1-(benzofuran-5-yl-sulfonyl)-4-((methylamino)methyl)-1H-pyrrole-2-yl)thiophene-2-carbonitrile trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(2-chlorothiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(furan-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(thiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(5-fluorothiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(3-methylthiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(5-methylthiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(4-methylthiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-7-yl-sulfonyl)-5-(thiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; N-methyl-1-(1-(thieno[3,2-b]pyridine-6-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)methaneamine trifluoroacetate; 1-(1-(benzofuran-6-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzo[b]thiophene-6-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzo[d]thiazole-6-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 6-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]thiazole-2(3H)-one trifluoroacetate; 3-methyl-5-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate; 1-(1-((2,3-dihydrobenzofuran-5-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 6-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate; 6-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)-2H-benzo[b][1,4]oxazine-3(4H)-one trifluoroacetate; 1-(1-((3,4-dihydro-2H-benzo[b][1,4]oxazine-7-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 5-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate; and 5-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate. In addition, the present invention provides a pharmaceutical composition for inhibiting potassium-competitive gastric acid secretion comprising a compound represented by the above formula I and a pharmaceutically acceptable salt thereof as an active ingredient. The pharmaceutical composition for inhibiting potassium-competitive gastric acid secretion according to the present invention may further comprise a pharmaceutically acceptable carrier, diluent, or excipient. In addition, the present invention provides a pharmaceutical composition for the prevention or treatment of a disease caused by gastric acid secretion disorder, comprising a compound represented by the above formula I or a pharmaceutically acceptable salt thereof as an active ingredient. Examples of diseases caused by the above gastric acid secretion disorder include, but are not limited to, gastrointestinal diseases, gastroesophageal diseases, gastroesophageal reflux disease (GERD), peptic ulcer, gastric ulcer, duodenal ulcer, NSAID-induced ulcer, gastritis, Helicobacter pylori infection, dyspepsia, functional dyspepsia, Zollinger-Ellison syndrome, non-erosive reflux disease (NERD), visceral referred pain, heartburn, nausea, esophagitis, dysphagia, drooling, airway obstruction, and asthma. The novel pyrrole derivative compounds of the present invention or pharmaceutically acceptable salts thereof reversibly inhibit the proton pump, thereby treating diseases caused by excessive secretion of gastric acid, particularly peptic ulcers, non-steroidal anti-inflammatory drug (NSAID)-induced ulcers, Helicobacter pylori infection, functional dyspepsia, Zollinger-Ellison syndrome, gastritis, gastric . It can be usefully applied to the prevention or treatment of esophageal reflux disease (GERD), non-erosive reflux disease (NERD), etc. Hereinafter, the present invention is described in detail with reference to examples to help a person skilled in the art to which the present invention pertains ("person skilled in the art") understand the present invention. However, the following examples are provided for the purpose of illustrating preferred embodiments of the present invention and should not be interpreted as limiting the scope of the present invention, and it will be obvious to a person skilled in the art that various modifications and applications of the following examples are possible. Synthesis of compounds of chemical formula (I) The following compounds were prepared using synthesis methods 1 to 5. Hereinafter, exemplary synthesis examples of some compounds of the present disclosure are described, and other compounds may be prepared in a manner similar to that described below using different starting materials or reactants. Synthesis Method 1 Example 1 1-(1-(benzofuran-5-ylsulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate Step 1) tert-butyl ((1-(benzofuran-5-ylsulfonyl)-5-bromo-1H-pyrrole-3-yl)methyl)(methyl)carbamate NaH (60% in oil, 228 mg) was added to a solution of tert-butyl ((5-bromo-1H-pyrrole-3-yl)methyl)(methyl)carbamate (550 mg) in DMF (9.5 mL) at 0°C. After stirring for 10 minutes at the same temperature, benzofuran-5-sulfonyl chloride (495 mg) was added, and the reaction was completed by stirring for 1 hour at room temperature. Water was added to the reaction mixture and purified by reverse-phase chromatography [gradient elution conditions of high-performance liquid chromatography (HPLC), in which a solvent mixed with water (containing 0.1% formic acid (FA)) and acetonitrile (containing 0.1% FA) in an 80:20 ratio is initially used, and the ratio of acetonitrile (containing 0.1% FA) increases to 100% over time] to obtain compound 3 (1.25 g, yield 81%) in the form of a pale yellow oil. 1 H NMR (400 MHz, DMSO-d6) δ 8.37 (d, J = 2.0 Hz, 1H), 8.25 (d, J = 2.3 Hz, 1H), 7.95 - 7.87 (m, 1H), 7.83 (dd, J = 8.8, 2.0 Hz, 1H), 7.51 (s, 1H), 7.18 (dd, J = 2.3, 0.9 Hz, 1H), 6.34 (s, 1H), 4.12 (s, 2H), 2.72 (s, 3H), 1.38 (s, 9H), [M+1]=469.37. Step 2) tert-butyl ((1-(benzofuran-5-ylsulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)methyl)(methyl)carbamate Under an argon atmosphere, compound 3 (40 mg), 4,4,5,5-tetramethyl-2-(thiophene-3-yl)-1,3,2-dioxaborolan (35.8 mg), Pd(dppf)Cl2·DCM (14 mg), and K2CO3 (35 mg) were added to a mixture of dioxane (0.28 mL) and water (0.12 mL), and then stirred at 100°C for 1 hour. After cooling the reaction mixture to room temperature, water was added and purified by reverse-phase chromatography [gradient elution conditions of high-performance liquid chromatography (HPLC), in which a solvent mixed with water (containing 0.1% formic acid (FA)) and acetonitrile (containing 0.1% FA) in an 80:20 ratio is initially used, and the ratio of acetonitrile (containing 0.1% FA) increases to 100% over time] to obtain compound 5 (33 mg, yield 82%) as a brown solid compound. 1 H NMR (400 MHz, DMSO-d6) δ 8.18 (d, J = 2.3 Hz, 1H), 7.78 (d, J = 2.1 Hz, 1H), 7.73 (d, J = 8.8 Hz, 1H), 7.51 (dd, J = 5.0, 3.0 Hz, 1H), 7.39 (d, J = 1.8 Hz, 1H), 7.33 (dd, J = 8.8, 2.1 Hz, 2H), 7.08 - 6.99 (m, 2H), 6.18 (s, 1H), 4.15 (s, 2H), 2.73 (s, 3H), 1.38 (s, 9H), [M+1]=473.40. Step 3) 1-(1-(benzofuran-5-ylsulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate TFA (0.35 mL) was added to a solution of Compound 5 (33 mg) in DCM (0.35 mL) at room temperature and stirred for 1 hour. The mixture was purified by reverse-phase chromatography [gradient elution conditions of high-performance liquid chromatography (HPLC), in which a solvent mixed with water (containing 0.1% formic acid (FA)) and acetonitrile (containing 0.1% FA) in an 80:20 ratio is initially used, and the ratio of acetonitrile (containing 0.1% FA) increases to 100% over time] to obtain Example 1 (19 mg, yield 56%) in the form of a pale yellow oil. 1 H NMR (400 MHz, DMSO-d6) δ8.61 (s, 2H), 8.21 (d, J = 2.4 Hz, 1H), 7.79 (d, J = 2Hz, 1H), 7.75 (d, J = 8.8Hz, 1H), 7.71 (d, J = 1.9Hz, 1H), 7.54 (dd, J = 3Hz, 5Hz, 1H), 7.36 (dd, J = 2.1 Hz, 8.8Hz, 1H), 7.31 (dd, J = 1.2 Hz, 3 Hz, 1H), 7.06 (dd, J = 0.8Hz, 2.2Hz, 1H), 6.97 (dd, J = 1.2 Hz, 5.0 Hz, 1H), 6.38 (d, 1.9Hz, 1H), 3.99 (t, J= 5.4Hz, 2H), 2.55 (t, J = 5.24 Hz, 3H), [M+1]=373.42 Examples 2~23 Compounds of Examples 2-23 were prepared as described in Table 2 below by using the synthesis method of Example 1, utilizing compound 3 of Step 1 as an intermediate, and changing the reactant to a substance similar to compound 4. Example Number Chemical Structure / Chemical Name NMR Data Molecular Weight [M+1]1 1-(1-(benzofuran-5-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.61 (s, 2H), 8.21 (d, J=2.4 Hz, 1H), 7.79 (d, J = 2 Hz, 1H), 7.75 (d, J = 8.8 Hz, 1H), 7.71 (d, J = 1.9 Hz, 1H), 7.54 (dd, J = 3 Hz, 5 Hz, 1H), 7.36 (dd, J = 2.1 Hz, 8.8 Hz, 1H), 7.31 (dd, J= 1.2 Hz, 3 Hz, 1H), 7.06 (dd, J = 0.8Hz, 2.2Hz, 1H), 6.97 (dd, J = 1.2 Hz, 5.0 Hz, 1H), 6.38 (d, 1.9Hz, 1H), 3.99 (t, J = 5.4Hz, 2H), 2.55 (t, J = 5.24Hz, 3H).373.352 1-(1-(benzofuran-5-yl-sulfonyl)-5-(5-methylthiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.58 (s, 2H), 8.22 (d, J = 2.22 Hz, 1H), 7.83 (d, J = 2.00 Hz, 1H), 7.77 (d, J = 8.81 Hz, 1H), 7.69 (d, J = 1.85 Hz, 1H), 7.40 (dd, J = 8.79, 2.07 Hz, 1H), 7.09 (dd, J = 2.21, 0.87 Hz, 1H), 7.04 (d, J = 1.44 Hz, 1H), 6.57 (t, J = 1.20, 1.22 Hz 1H), 6.33 (d, J = 1.91 Hz, 1H), 3.98 (s, 2H), 2.54 (s, 3H), 2.39 (d, J = 0.93 Hz, 3H).387.383 1-(1-(benzofuran-5-yl-sulfonyl)-5-(4-methylthiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.62 (s, 2H), 8.23 ​​(d, J = 2.22 Hz, 1H), 7.77 (d, J = 8.79 Hz, 1H), 7.72 (dd, J = 14.80, 1.89 Hz, 2H), 7.37 (dd, J = 8.77, 2.06 Hz, 1H), 7.18 (d, J = 3.16 Hz, 1H), 7.10 (dd, J = 3.16, 1.05 Hz, 1H), 7.08 (dd, J = 2.22, 0.88 Hz, 1H), 6.29 (d, J = 1.87 Hz, 1H), 4.01 (s, 2H), 2.55 (s, 3H), 1.59 (d, J = 0.57 Hz, 3H).387.384 1-(1-(benzofuran-5-yl-sulfonyl)-5-(2-methylthiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.64 (s, 2H), 8.23 ​​(d, J = 2.22 Hz, 1H), 7.78 (d, J = 8.78 Hz, 1H), 7.75 (d, J = 1.80 Hz, 1H), 7.67 (d, J = 1.97 Hz, 1H), 7.36 (dd, J = 8.77, 2.06 Hz, 1H), 7.31 (d, J = 5.23 Hz, 1H), 7.08 (dd, J = 2.20, 0.84 Hz, 1H), 6.79 (d, J = 5.24 Hz, 1H), 6.28 (d, J = 1.87 Hz, 1H), 4.01 (t, J = 4.82, 4.84 Hz, 2H), 2.55 (t, J = 4.77, 4.90 Hz, 3H), 1.61 (s, 3H).387.385 1-(1-(benzofuran-5-yl-sulfonyl)-4-(2,5-dimethylthiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.62 (s, 2H), 8.23 ​​(d, J = 2.22 Hz, 1H), 7.79 (d, J = 8.78 Hz, 1H), 7.72 (dd, J = 1.88, 4.37 Hz, 2H), 7.40 (dd, J = 2.05, 8.77 Hz, 1H), 7.10 (dd, J = 0.85, 2.21 Hz, 1H), 6.32 (d, J = 1.00 Hz, 1H), 6.23 (d, J = 1.87 Hz, 1H), 4.00 (s, 2H), 2.54 (s, 3H), 2.32 (s, 3H), 1.60 (s, 3H).401.486 4-(1-(benzofuran-5-yl-sulfonyl)-4-((methylamino)methyl)-1H-pyrrole-2-yl)thiophene-2-carbonitrile trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.69-8.53 (bs, 2H), 8.24 (d, J = 2.4 Hz, 1H), 7.85-7.76 (m, 5H), 7.39 (dd, J = 2.0, 8.8 Hz, 1H), 7.10 (dd, J = 1.0, 2.2 Hz, 1H), 6.47 (d, J = 2.0 Hz, 1H), 3.99 (s, 2H), 2.54 (s, 3H) 398.297 1-(1-(benzofuran-5-yl-sulfonyl)-5-(2-chlorothiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.62 (s, 2H), 8.23 ​​(d, J = 2.23 Hz, 1H), 7.81-7.78 (m, 3H), 7.52 (d, J = 5.72 Hz, 1H), 7.42 (dd, J = 8.74, 2.12 Hz, 1H), 7.09 (dd, J = 2.21, 0.82 Hz, 1H), 6.94 (d, J = 5.73 Hz, 1H), 6.42 (d, J = 1.85 Hz, 1H), 4.02 (s, 2H), 2.55 (s, 3H).407.458 1-(1-(benzofuran-5-yl-sulfonyl)-5-(isothiazole-4-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.87 (s, 1H), 8.63 (s, 2H), 8.37 (s, 1H), 8.22 (d, J = 2.23 Hz, 1H), 7.82 (d, J = 2.02 Hz, 1H), 7.79 - 7.77 (m, 2H), 7.36 (dd, J = 2.09, 8.79 Hz, 1H), 7.08 (dd, J = 0.87, 2.21 Hz, 1H), 6.50 (d, J = 1.88 Hz, 1H), 4.00 (t, J = 5.09 Hz, 2H), 2.55 (t, J = 5.1 Hz, 3H).374.369 1-(1-(benzofuran-5-yl-sulfonyl)-5-(furan-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.61 (s, 2H), 8.22 (d, J = 2.2 Hz, 1H), 7.98 (d, J = 2 Hz, 1H), 7.80 (d, J= 8.8 Hz, 1H), 7.72 (d, J= 1.9 Hz, 1H), 7.70 (t, J= 1.7 Hz, 1H), 7.64 (m, 1H), 7.48 (dd, J= 2.0 Hz, 8.8 Hz, 1H), 7.10 (dd, J = 0.9 Hz, 2.2Hz, 6.47 (dd, J= 0.7 Hz, 1.8Hz, 1H), 6.41 (d, J = 1.9Hz, 1H), 3.98 (t, J= 5.3 Hz, 2H), 2.54 (t, J = 5.1 Hz, 3H).357.3410 1-(1-(benzofuran-5-ylsulfonyl)-5-(2,5-dimethylfuran-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.68-8.51 (bs, 2H), 8.23 ​​(d, J = 2.4 Hz, 1H), 7.88 (d, J = 2.0 Hz, 1H), 7.81 (d, J = 8.8 Hz, 1H), 7.70 (d, J = 2.0 Hz, 1H), 7.45 (dd, J = 2.0, 8.8 Hz, 1H), 7.13 (dd, J = 1.0, 2.2 Hz, 1H), 6.23 (d, J = 2.0 Hz, 1H), 5.86 (d, J = 0.8 Hz, 1H), 3.98 (s, 2H), 2.54 (s, 3H), 2.23 (s, 3H), 1.60 (s, 3H),385.3211 1-(1-(benzofuran-5-yl-sulfonyl)-5-(1H-pyrazole-4-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.58 (br s, 2H), 7.85 (d, J = 2.22 Hz, 1H), 7.76 (d, J = 7.76 Hz, 1H), 7.68 (d, J = 1.83 Hz, 1H), 7.51 (br s, 2H), 7.37 (dd, J = 8.8, 2.0 Hz, 1H), 7.07 (m, 1H), 6.32 (d, J = 1.9 Hz, 1H), 3.98 (t, J = 5.5 Hz, 2H), 2.54 (t, J = 5.3 Hz, 3H).357.3412 1-(1-(benzofuran-5-yl-sulfonyl)-5-(1-methyl-1H-pyrazole-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.62 (s, 2H), 8.24 (d, J = 2.3 Hz, 1H), 8.07 (d, J = 2.1 Hz, 1H), 7.82 (d, J = 8.8 Hz, 1H), 7.74 - 7.68 (m, 2H), 7.63 (dd, J = 8.8, 2.1 Hz, 1H), 7.15 (dd, J = 2.3, 0.9 Hz, 1H), 6.46 (d, J = 2.0 Hz, 1H), 6.32 (d, J = 2.2 Hz, 1H), 4.01 (t, J = 5.3 Hz, 2H), 3.78 (s, 3H), 2.56 (t, J = 5.0 Hz, 3H).371.3713 Ethyl 2-(4-(1-(benzofuran-5-yl-sulfonyl)-4-((methylamino)methyl)-1H-pyrrole-2-yl)-1H-pyrazole-1-yl)acetate trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.60 (br s, 2H), 8.21 (d, J = 2.2 Hz, 1H), 7.93 (d, J = 2.0 Hz, 1H), 7.82 (s, 1H), 7.74 (d, J = 8.8 Hz, 1H), 7.69 (d, J = 1.8 Hz, 1H), 7.48 (dd, J = 8.7, 2.0 Hz, 1H), 7.3 (s, 1H), 7.05 (m, 1H), 6.34 (d, J = 1.9 Hz, 1H), 5.13 (s, 2H), 4.24 (q, J = 7.1 Hz, 2H), 3.98 (t, J = 4.98 Hz, 2H), 2.55 (t, J = 4.98 Hz, 3H), 1.27 (t, J = 7.1 Hz, 3H).443.4114 1-(1-(benzofuran-5-yl-sulfonyl)-5-(furan-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.64 (s, 2H), 8.24 (d, J = 2.2 Hz, 1H), 8.12 (d, J = 2.1 Hz, 1H), 7.84 (d, J = 8.8 Hz, 1H), 7.78 (d, J = 1.9 Hz, 1H), 7.70 (d, J = 1.9 Hz, 1H), 7.63 (dd, J = 8.8, 2.1 Hz, 1H), 7.14 (d, J = 2.2 Hz, 1H), 6.64 - 6.57 (m, 2H), 6.57 - 6.52 (m, 1H), 4.00 (s, 2H), 2.55 (s, 3H)357.3415 1-(1-(benzofuran-5-yl-sulfonyl)-5-(thiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.63 (s, 2H), 8.21 (d, J = 2.2 Hz, 1H), 7.84 (d, J = 2 Hz, 1H), 7.79 (d, J=1.8 Hz, 1H), 7.76 (d, J=8.8 Hz, 1H), 7.57 (dd, J=1.3 Hz, 5.0 Hz, 1H), 7.40 (dd, J=2.0 Hz, 8.8 Hz, 1H), 7.10–7.06 (m, 3H), 6.48 (d, J=1.9 Hz, 1H), 4.00 (m,2H), 2.56 (m,3H).373.3516 1-(4-(1-(benzofuran-5-yl-sulfonyl)-4-((methylamino)methyl)-1H-pyrrole-2-yl)thiophene-2-yl)ethane-1-one trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.70-8.56 (m, 2H), 8.22 (d, J = 2.4 Hz, 1H), 7.86 (d, J = 2.0 Hz, 1H), 7.80 (d, J = 8.4 Hz, 1H), 7.76 (t, J = 1.6, 1.2 Hz, 2H), 7.57 (d, J = 1.2 Hz, 1H), 7.42 (dd, J = 8.8, 2.0 Hz, 1H), 7.07 (dd, J = 2.0, 0.80 Hz, 1H), 6.45 (d, J = 2.0 Hz, 1H), 4.04-3.97 (bs, 2H), 2.58-2.53 (bs, 3H), 2.43 (s, 3H)415.3517 4-(1-(benzofuran-5-yl-sulfonyl)-4-((methylamino)methyl)-1H-pyrrole-2-yl)thiophene-2-carboxamide trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.67-8.53 (bs, 2H), 8.22 (d, J = 2.4 Hz, 1H), 7.93-7.85 (bs, 1H), 7.82 (d, J = 2.0 Hz, 1H), 7.77 (d, J = 8.8 Hz, 1H), 7.72 (d, J = 2.0 Hz, 1H), 7.60 (d, J = 1.2 Hz, 1H), 7.47 (d, J = 1.2 Hz, 1H), 7.44-7.35 (m, 2H), 7.06 (dd, J = 1.0, 2.2 Hz, 1H), 6.39 (d, J = 2.0 Hz, 1H), 3.99 (s, 2H), 2.54 (s, 3H)416.3418 1-(1-(benzofuran-5-yl-sulfonyl)-5-(5-fluorothiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.67-8.55 (m, 2H), 8.24 (d, J = 2.0 Hz, 1H), 7.95 (d, J = 2.0 Hz, 1H), 7.82 (d, J = 8.8 Hz, 1H), 7.79 (d, J = 1.6 Hz, 1H), 7.48 (dd, J = 8.8, 2.0 Hz, 1H), 7.11 (dd, J = 2.4, 0.8 Hz, 1H), 6.74-6.69 (m, 2H), 6.51 (d, J = 2.0 Hz, 1H), 3.99 (s, 2H), 2.55 (s, 3H)391.2919 1-(1-(benzofuran-5-yl-sulfonyl)-5-(3-methylthiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.63 (s, 2H), 8.23 ​​(d, J = 2.3 Hz, 1H), 7.84 - 7.76 (m, 3H), 7.54 (d, J = 5.1 Hz, 1H), 7.43 (dd, J = 8.8, 2.1 Hz, 1H), 7.09 (dd, J = 2.3, 0.9 Hz, 1H), 6.87 (d, J = 5.1 Hz, 1H), 6.41 (d, J = 1.9 Hz, 1H), 4.02 (t, J = 5.6 Hz, 2H), 2.56 (t, J = 5.3 Hz, 3H), 1.63 (s, 3H).387.4520 1-(1-(benzofuran-5-yl-sulfonyl)-5-(5-methylthiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.20 (d, J = 2.2 Hz, 1H), 7.85 (d, J = 2.1 Hz, 1H), 7.76 (d, J = 8.7 Hz, 1H), 7.49 - 7.39 (m, 2H), 7.09 (d, J = 2.3 Hz, 1H), 6.83 (d, J = 3.5 Hz, 1H), 6.77 (dd, J = 3.5, 1.3 Hz, 1H), 6.30 (d, J = 1.9 Hz, 1H), 3.53 (s, 2H), 2.39 (s, 3H), 2.28 (s, 3H).387.4521 1-(1-(benzofuran-5-yl-sulfonyl)-5-(4-methylthiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.20 (d, J = 2.2 Hz, 1H), 7.87 (d, J = 2.1 Hz, 1H), 7.76 (d, J = 8.8 Hz, 1H), 7.51 (d, J = 1.9 Hz, 1H), 7.43 (dd, J = 8.8, 2.1 Hz, 1H), 7.10 (d, 2H), 6.79 (d, J = 1.5 Hz, 1H), 6.34 (d, J = 1.9 Hz, 1H), 3.57 (s, 2H), 2.30 (s, 3H), 2.20 (s, 3H).387.4922 1-(1-(benzofuran-7-yl-sulfonyl)-5-(thiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.66 (s, 2H), 8.10 (d, J = 2.2 Hz, 1H), 8.08 - 8.01 (m, 1H), 7.92 (d, J = 1.9 Hz, 1H), 7.52 (dd, J = 5.1, 1.2 Hz, 1H), 7.35 - 7.26 (m, 2H), 7.15 (d, J = 2.2 Hz, 1H), 7.02 (dd, J = 5.2, 3.6 Hz, 1H), 6.96 (dd, J = 3.6, 1.2 Hz, 1H), 6.49 (d, J = 2.0 Hz, 1H), 4.05 (s, 2H), 2.57 (s, 3H).373.3923 N-methyl-1-(1-(thieno[3,2-b]pyridine-6-ylsulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)methaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.71 (br, 2H), 8.66 (s, 1H), 8.56 (d, J = 5.6 Hz, 1H), 8.50 (d, J = 2.4 Hz, 1H), 7.75 (d, J = 1.6 Hz, 1H), 7.69 (dd, J = 5.4, 0.6 Hz, 1H), 7.57 (dd, J = 5.0, 3.0 Hz, 1H), 7.36 (dd, J = 3.2, 1.2 Hz, 1H), 7.00 (dd, J = 5.2, 1.2 Hz, 1H), 6.42 (d, J = 2.0 Hz, 1H), 4.00 (s, 2H), 2.55 (s, 3H)390.30 Synthesis Method 2 Example 24 1-(1-(benzofuran-5-ylsulfonyl)-5-(thiazole-5-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate Step 1) tert-butyl ((1-(benzofuran-5-ylsulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)methyl)(methyl)carbamate Under an argon atmosphere, tert-butyl ((5-bromo-1H-pyrrole-3-yl)methyl)(methyl)carbamate (150 mg), 5-(4,4,5,5-tetramethyl-1,3,2-dioxbororan-2-yl)thiazole (40 mg), Xphos Pd G4 (44 mg) and K2CO3 (236 mg) were added to a mixture of dioxane (2 mL) and water (0.5 mL), and then stirred at 100°C for 1 hour. After cooling the reaction mixture to room temperature, water was added and purified by reverse-phase chromatography [gradient elution conditions of high-performance liquid chromatography (HPLC), in which a solvent mixed with water (containing 0.1% formic acid (FA)) and acetonitrile (containing 0.1% FA) in an 80:20 ratio is initially used, and the ratio of acetonitrile (containing 0.1% FA) increases to 100% over time] to obtain compound 7 (33 mg, yield 21%) as a brown solid compound. 1 H NMR (400 MHz, DMSO) δ 11.33 (s, 1H), 8.86 (d, J = 0.7 Hz, 1H), 7.98 (d, J = 0.7 Hz, 1H), 6.78 (d, J = 2.2 Hz, 1H), 6.26 (s, 1H), 4.15 (s, 2H), 2.73 (s, 3H), 1.43 (s, 9H), [M+1]=294.35. Step 2) tert-butyl ((1-(benzofuran-5-ylsulfonyl)-5-(thiazole-5-yl)-1H-pyrrole-3-yl)methyl)(methyl)carbamate Compound 7 (33 mg) was dissolved in DMF (0.55 mL), and NaH (60% in oil, 228 mg) was added at 0°C. After stirring for 10 minutes at the same temperature, benzofuran-5-sulfonyl chloride (40 mg) was added, and the reaction was completed by stirring at room temperature for 1 hour. Water was added to the reaction mixture, and the mixture was purified by reverse-phase chromatography [a gradient elution condition of high-performance liquid chromatography (HPLC), in which a solvent mixture of water (containing 0.1% formic acid (FA)) and acetonitrile (containing 0.1% FA) in an 80:20 ratio is initially used, and the proportion of acetonitrile (containing 0.1% FA) increases to 100% over time] to obtain Compound 8 (48 mg, yield 90%) in the form of a pale yellow oil. 1 H NMR (400 MHz, DMSO-d6) δ 9.12 (s, 1H), 8.21 (d, J = 2.2 Hz, 1H), 7.90 (d, J = 2.1 Hz, 1H), 7.79 (d, J = 8.8 Hz, 1H), 7.74 (s, 1H), 7.54 (s, 1H), 7.42 (dd, J = 8.8, 2.1 Hz, 1H), 7.09 (dd, J = 2.2, 0.9 Hz, 1H), 6.39 (s, 1H), 5.74 (s, 1H), 4.18 (s, 2H), 3.21 (s, 3H), 2.75 (s, 3H), 1.37 (s, 9H), [M+1]=474.58. Step 3) 1-(1-(benzofuran-5-ylsulfonyl)-5-(thiazole-5-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate TFA (0.35 mL) was added to a solution of Compound 8 (33 mg) in DCM (0.35 mL) at room temperature and stirred for 1 hour. The mixture was purified by reverse-phase chromatography [gradient elution conditions of high-performance liquid chromatography (HPLC), in which a solvent mixed with water (containing 0.1% formic acid (FA)) and acetonitrile (containing 0.1% FA) in an 80:20 ratio is initially used, and the ratio of acetonitrile (containing 0.1% FA) increases to 100% over time] to obtain Example 24 (28 mg, yield 56%) in the form of a pale yellow oil. 1 H NMR (400 MHz, DMSO-d6) δ 9.15 (d, J = 0.8 Hz, 1H), 8.63 (s, 2H), 8.24 (d, J = 2.2 Hz, 1H), 7.92 (d, J = 2.1 Hz, 1H), 7.88 - 7.78 (m, 2H), 7.71 (d, J = 0.8 Hz, 1H), 7.44 (dd, J = 8.8, 2.1 Hz, 1H), 7.10 (dd, J = 2.3, 1.0 Hz, 1H), 6.59 (d, J = 1.9 Hz, 1H), 4.01 (t, J = 5.6 Hz, 2H), 2.56 (t, J = 5.4 Hz, 3H), [M+1]=374.41 Examples 25-41 Compounds of Examples 25-41 were prepared as described in Table 2 below by using the synthesis method of Example 24, utilizing compound 7 of Step 1 as an intermediate, and changing the reactant to a substance similar to compound 2. Example Number Chemical Structure / Chemical Name NMR Data Molecular Weight [M+1] 24 1-(1-(benzofuran-5-yl-sulfonyl)-5-(thiazole-5-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 9.15 (d, J = 0.8 Hz, 1H), 8.63 (s, 2H), 8.24 (d, J = 2.2 Hz, 1H), 7.92 (d, J = 2.1 Hz, 1H), 7.88 - 7.78 (m, 2H), 7.71 (d, J = 0.8 Hz, 1H), 7.44 (dd, J = 8.8, 2.1 Hz, 1H), 7.10 (dd, J = 2.3, 1.0 Hz, 1H), 6.59 (d, J = 1.9 Hz, 1H), 4.01 (t, J = 5.6 Hz, 2H), 2.56 (t, J = 5.4 Hz, 3H)374.4125 1-(1-(benzofuran-6-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1 H NMR (400 MHz, DMSO-d6) δ 8.70-8.57 (m, 2H), 8.30 (d, J = 2.2 Hz, 1H), 7.80 (d, J = 8.3 Hz, 1H), 7.72 (d, J = 1.7 Hz, 1H), 7.63-7.61 (bs, 1H), 7.55 (dd, J = 5.0, 3.0 Hz, 1H), 7.33 (d, J = 1.4 Hz, 1H), 7.32 (dd, J = 5.0, 1.4 Hz, 1H), 7.12 (d, J = 1.4 Hz, 1H), 6.99 (dd, J = 5.0, 1.2 Hz, 1H), 6.38 (d, J = 1.9 Hz, 1H), 3.99 (s, 2H), 2.56-2.53 (bs, 3H)373.2326 1-(1-(benzofuran-5-yl-sulfonyl)-5-(5-(trifluoromethyl)thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.64 (bs, 2H), 8.23 ​​(d, J = 2.0 Hz, 1H), 7.83 (d, J = 2.0 Hz, 1H), 7.80-7.76 (m, 2H), 7.74 (d, J = 1.6 Hz, 1H), 7.42-7.40 (m, 1H), 7.38 (dd, J = 8.6, 2.2 Hz, 1H), 7.06 (dd, J = 2.0, 0.8 Hz, 1H), 6.48 (d, J = 2.0 Hz, 1H), 4.04-.396 (bs, 2H), 2.58-2.52 (bs, 3H)441.2827 1-(1-(benzo[b]thiophene-6-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1 H NMR (400 MHz, DMSO-d6) δ 8.64 (s, 2H), 8.17-8.14 (m, 2H), 7.99 (d, J = 8.53 Hz, 1H), 7.72 (d, J = 1.84 Hz, 1H), 7.58 (d, J = 5.42 Hz, 1H), 7.54 (dd, J = 2.99, 4.97 Hz, 1H), 7.36 (dd, J = 1.81, 8.53 Hz, 1H), 7.32 (dd, J = 1.26, 2.97 Hz, 1H), 6.98 (dd, J = 1.25, 4.98 Hz, 1H), 6.38 (d, J = 1.90 Hz, 1H), 3.99 (s, 2H), 2.55 (s, 3H)389.2428 1-(1-(benzo[d]thiazole-6-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 9.68 (s, 1H), 8.62 (s, 2H), 8.36 (d, J = 1.90 Hz, 1H), 8.18 (d, J = 8.71 Hz, 1H), 7.74 (d, J = 1.87 Hz, 1H), 7.53 (dd, J = 3.00, 4.99 Hz, 1H), 7.50 (dd, J = 2.04, 8.72 Hz, 1H), 7.31 (dd, J = 1.28, 2.97 Hz, 1H), 6.96 (dd, J = 1.27, 4.98 Hz, 1H), 6.39 (d, J = 1.90 Hz, 1H), 4.00 (s, 2H), 2.55 (s, 3H)390.2329 1-(1-((2,2-difluorobenzo[d][1,3]dioxol-4-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1 H NMR (400 MHz, DMSO-d6) δ 8.72-8.59 (bs, 2H), 7.78-7.74 (m, 2H), 7.52 (dd, J = 5.0, 3.0 Hz, 1H), 7.34 (dd, J = 2.8, 1.2 Hz, 1H), 7.29 (t, J) = 8.0, 8.4 Hz, 1H), 7.05 (dd, J = 8.4, 0.8 Hz, 1H), 6.93 (dd, J = 5.0, 1.4 Hz, 1H), 6.47 (d, J = 1.6 Hz, 1H), 4.04 (t, J = 5.2, 5.2 Hz, 2H), 2.55 (t, J = 5.4, 5.4 Hz, 3H)413.2330 6-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]thiazole-2(3H)-one trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 12.49 (s, 1H), 8.63 (s, 2H), 7.68 (d, J = 2.0 Hz, 1H), 7.65 (d, J = 1.8 Hz, 1H), 7.56 (dd, J = 2.9, 4.9 Hz, 1H), 7.34 (dd, J = 1.2, 2.9 Hz, 1H), 7.29 (dd, J = 2.0, 8.5 Hz, 1H), 7.14 (d, J = 8.5 Hz, 1H), 6.99 (dd, J = 1.2, 4.9 Hz, 1H), 6.39 (d, J = 1.9) Hz, 1H), 3.99 (s, 2H), 2.55 (s, 3H)406.1231 3-methyl-6-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]thiazole-2(3H)-one trifluoroacetate 1 H NMR (400 MHz, CDCl3) δ 7.57 (d, J = 2.0 Hz, 1H), 7.37 (dd, J = 8.6, 1.8 Hz, 1H), 7.32 (d, J = 2.0 Hz, 1H), 7.28-7.26 (m, 1H), 7.13 (dd, J = 2.8, 1.2 Hz, 1H), 7.00 (dd, J = 4.8, 1.2 Hz, 1H), 6.94 (d, J = 8.8 Hz, 1H), 6.28 (d, J = 2.0 Hz, 1H), 3.94 (s, 2H), 3.43 (s, 3H), 2.61 (s, 3H)420.3032 6-((2-(isothiazole-4-yl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]thiazole-2(3H)-one trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 12.51 (s, 1H), 8.89 (s, 1H), 8.72-8.58 (bs, 2H), 8.40 (s, 1H), 7.79 (d, J = 2.0 Hz, 1H), 7.72 (d, J = 1.7 Hz, 1H), 7.28 (dd, J = 8.6, 2.1 Hz, 1H), 7.17 (d, J = 8.5 Hz, 1H), 6.52 (d, J = 1.9 Hz, 1H), 4.01 (s, 2H), 2.58-2.53 (bs, 3H)407.1833 3-methyl-5-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate 1 H NMR (400 MHz, DMSO-d6) δ 8.68 (br, 2H), 7.69 (d, J = 2.0 Hz, 1H), 7.58 (dd, J = 5.0, 3.0 Hz, 1H), 7.47 (d, J = 8.4 Hz, 1H), 7.33 (dd, J = 2.8, 1.2 Hz, 1H), 7.24 (dd, J = 8.4, 2.0 Hz, 1H), 7.14 (d, J = 2.0 Hz, 1H), 7.00 (dd, J = 4.8, 1.2 Hz, 1H), 6.39 (d, J = 2.0 Hz, 1H), 3.99 (s, 2H), 3.28 (s, 3H), 2.55 (s, 3H)404.3034 1-(1-((2,3-dihydrobenzofuran-5-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.77 (br, 2H), 7.63 (d, J = 1.6 Hz, 1H), 7.57 (dd, J = 5.0, 3.0 Hz, 1H), 7.35 (dd, J = 2.8, 1.2 Hz, 1H), 7.20-7.18 (m, 2H), 7.00 (dd, J = 5.2, 1.2 Hz, 1H), 6.82 (dd, J = 5.6, 3.6 Hz, 1H), 6.37 (d, J = 2.0 Hz, 1H), 4.64 (t, J = 9.0 Hz, 2H), 3.98 (s, 2H), 3.14 (t, J = 8.8 Hz, 2H), 2.54 (s, 3H)375.3035 3,3-dimethyl-5-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)indolin-2-one trifluoroacetate 1 H NMR (400 MHz, CDCl3) δ 7.57 (d, J = 2.0 Hz, 1H), 7.18 (dd, J = 8.2, 1.8 Hz, 1H), 7.10-7.08 (m, 2H), 6.95 (d, J = 2.0 Hz, 1H), 6.87 (d, J = 8.4 Hz, 1H), 6.67 (d, J = 4.8 Hz, 1H), 6.20 (d, J = 1.6 Hz, 1H), 3.93 (s, 2H), 2.72 (s, 3H), 1.21 (s, 6H)416.4036 1,3-dimethyl-5-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)-1,3-dihydro-2H-benzo[d]imidazole-2-one trifluoroacetate 1H NMR (400 MHz, CDCl3) δ 9.70 (br, 2H), 7.58 (d, J = 2.0 Hz, 1H), 7.25-7.22 (m, 2H), 7.14 (dd, J = 3.2, 1.2 Hz, 1H), 7.03 (dd, J = 5.2, 1.2 Hz, 1H), 6.88-6.85 (m, 2H), 6.26 (d, J = 1.6 Hz, 1H), 3.93 (s, 2H), 3.39 (s, 3H), 3.30 (s, 3H), 2.59 (s, 3H)417.4037 6-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate 1 H NMR (400 MHz, DMSO-d6) δ 12.45-12.24 (bs, 1H), 8.75-8.52 (bs, 2H), 7.75 (d, J = 1.6 Hz, 1H), 7.57-7.50 (m, 1H), 7.30 (d, J = 2.0 Hz, 1H), 7.27-7.18 (m, 4H), 7.07 (td, J = 7.4, 7.60, 1.8 Hz, 1H), 6.42 (d, J = 2.0 Hz, 1H), 4.00 (s, 2H), 2.56 (s, 3H)402.2338 6-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]thiazole-2(3H)-one trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 12.52 (s, 1H), 8.70-8.59 (bs, 2H), 7.71 (t, J = 1.6, 1.6 Hz, 2H), 7.55-7.49 (m, 1H), 7.31 (dd, J = 8.8, 2.0 Hz, 1H), 7.23-7.17 (m, 3H), 7.07 (td, J = 7.4, 7.4, 1.6 Hz, 1H), 6.42 (d, J = 1.6 Hz, 1H), 4.01 (t, J = 5.4, 5.4 Hz, 2H), 2.56 (t, J = 5.2, 5.2Hz, 3H)418.1339 1-(1-(benzo[d][1,3]dioxol-5-ylsulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1 H NMR (400 MHz, DMSO-d6) δ 8.62 (br, 2H), 7.64 (d, J = 2.0 Hz, 1H), 7.57 (dd, J = 5.0, 3.0 Hz, 1H), 7.38 (dd, J = 2.8, 1.2 Hz, 1H), 7.02-6.95 (m, 3H), 6.84 (d, J = 1.6 Hz, 1H), 6.39 (d, J = 2.0 Hz, 1H), 6.16 (s, 2H), 3.98 (s, 2H), 2.55 (s, 3H)377.4040 1-(1-(indolin-5-ylsulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.65 (br, 2H), 7.57-7.55 (m, 2H), 7.36 (dd, J = 3.0, 1.0 Hz, 1H), 7.03 (dd, J = 5.0, 1.0 Hz, 1H), 6.96 (dd, J = 5.0, 1.0 Hz, 1H) 8.4, 2.0 Hz, 1H), 6.85 (s, 1H), 6.80 (br, 1H), 6.33-6.29 (m, 2H), 3.97 (s, 2H), 3.53 (t, J = 8.8 Hz, 2H), 2.87 (t, J = 8.8 Hz, 2H), 2.54 (s, 3H)374.5041 1-(1-((2,3-dihydro-1H-indene-5-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1 H NMR (400 MHz, DMSO-d6) δ 8.64 (br, 2H), 7.65 (d, J = 1.6 Hz, 1H), 7.57 (dd, J = 5.0, 3.0 Hz, 1H), 7.35-7.34 (m, 2H), 7.22-7.18 (m, 2H), 6.99 (dd, J = 4.8, 1.2 Hz, 1H), 6.37 (d, J = 2.0 Hz, 1H), 3.98 (s, 2H), 2.88 (t, J = 7.4 Hz, 2H), 2.81 (t, J = 7.6 Hz, 2H), 2.54 (s, 3H), 2.05-1.97 (m, 2H)373.40 Synthesis Method 3 Example 42 6-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)-2H-benzo[b][1,4]oxazine-3(4H)-one trifluoroacetate Step 1) tert-butylmethyl((5-(thiophene-3-yl)-1H-pyrrole-3-yl)methyl)carbamate Under an argon atmosphere, tert-butyl ((5-bromo-1H-pyrrole-3-yl)methyl)(methyl)carbamate (1000 mg), 4,4,5,5-tetramethyl-2-(thiophene-3-yl)-1,3,2-dioxaborolan (1090 mg), Pd(dppf)Cl2.DCM (350 mg) and K2CO3 (477 mg) were added to a mixture of dioxane (14 mL) and water (3.5 mL), and then stirred at 100°C for 1 hour. After cooling the reaction mixture to room temperature, water was added and purified by reverse-phase chromatography [gradient elution conditions of high-performance liquid chromatography (HPLC), in which a solvent mixed with water (containing 0.1% formic acid (FA)) and acetonitrile (containing 0.1% FA) in an 80:20 ratio is initially used, and the ratio of acetonitrile (containing 0.1% FA) increases to 100% over time] to obtain compound 9 (760 mg, yield 75.3%) as a solid compound. 1 H NMR (400 MHz, DMSO-d6) δ 11.01 (s, 1H), 7.52 (dd, J = 5.2, 2.8 Hz, 1H), 7.48 (dd, J = 2.8, 1.2 Hz, 1H), 7.35 (dd, J = 5.0, 1.4 Hz, 1H), 6.68-6.66 (m, 1H), 6.25 (s, 1H), 4.15 (s, 2H), 2.72 (s, 3H), 1.43 (s, 9H), [M+1]=293.21. Step 2) tert-butyl ((1-((4-hydroxy-3-nitrophenyl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)methyl)(methyl)carbamate Compound 9 (143 mg) was dissolved in a DMF (2.5 mL) solution, and NaH (60% in oil, 97 mg) was added at 0°C. After stirring for 30 minutes at the same temperature, 4-hydroxy-3-nitrobenzenesulfonyl chloride (116 mg) was slowly added over 5 minutes. Then, the reaction was completed by stirring at room temperature for 1 hour. After terminating the reaction by adding water to the reaction mixture, the mixture was extracted twice with CH2Cl2, dried with Na2SO4, and concentrated under reduced pressure. The reaction compound was purified by reverse-phase chromatography [high-performance liquid chromatography (HPLC) gradient elution conditions, in which a solvent mixed with water (containing 0.1% formic acid (FA)) and acetonitrile (containing 0.1% FA) in an 80:20 ratio is initially used, and the ratio of acetonitrile (containing 0.1% FA) increases to 100% over time] to obtain compound 11 (178 mg, yield 73.9%) in the form of a pale yellow solid. 1 H NMR (400 MHz, DMSO-d6)δ 7.74 (d, J = 2.4 Hz, 1H), 7.53 (dd, J = 3.0, 5.0 Hz, 1H), 7.48 (dd, J = 1.6, 8.4 Hz, 1H), 7.40 (d, J = 2.0 Hz, 1H), 7.36 (d, J = 1.6 Hz, 1H), 7.12 (d, J = 8.8 Hz, 1H), 7.05 (dd, J = 1.2, 4.8 Hz, 1H), 6.21 (s, 1H), 4.16 (s, 2H), 2.74 (s, 3H), 1.39 (s, 9H), [M+1]=494.27. Step 3) Ethyl 2-(4-((4-(((tert-butoxycarbonyl)(methyl)amino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)-2-nitrophenoxy)acetate Compound 11 (29 mg, 1.0 equivalent) was dissolved in DMF (0.3 mL, 0.2 M) and stirred at room temperature, after which K2CO3 (24.8 mg, 3.0 equivalent) and ethyl 2-bromoacetate (7.27 μL, 1.1 equivalent) were added and reacted at room temperature for 48 hours. The reaction compound was purified by reverse-phase chromatography [a gradient elution condition of high-performance liquid chromatography (HPLC), in which a solvent mixture of water (containing 0.1% formic acid (FA)) and acetonitrile (containing 0.1% FA) in an 80:20 ratio was initially used, and the ratio of acetonitrile (containing 0.1% FA) increased to 100% over time] to obtain Compound 13 (19 mg, yield 57.4%) in solid form. 1 H NMR (400 MHz, DMSO-d6) δ 7.81 (d, J = 2.0 Hz, 1H), 7.62 (dd, J = 2.4, 9.2 Hz, 1H), 7.55 (dd, J = 3.2, 4.8 Hz, 1H), 7.44 (d, J = 9.2 Hz, 1H), 7.41-7.37 (m, 2H), 7.04 (dd, J = 1.0, 5.0 Hz, 1H), 6.23 (s, 1H), 4.19-4.13 (m, 4H), 2.73 (s, 3H), 1.39 (s, 9H), 4.16 (t, J = 7.2 Hz, 3H), [M+1]=580.37. Step 4) Ethyl 2-(2-amino-4-((4-(((tert-butoxycarbonyl)(methyl)amino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)phenoxy)acetate Compound 13 (160.0 mg, 1.0 equivalent) was dissolved in DMSO (2.16 mL, 0.15 M), to which B2(OH)4 (87.2 mg, 3.0 equivalent) and 4,4-bipyridine (4.4 mg, 5 mol%) were added and stirred at room temperature. After the reaction was complete, the mixture was purified by reverse-phase chromatography [high-performance liquid chromatography (HPLC) gradient elution conditions, in which a solvent mixture of water (containing 0.1% formic acid (FA)) and acetonitrile (containing 0.1% FA) in an 80:20 ratio was initially used, and the proportion of acetonitrile (containing 0.1% FA) increased to 100% over time] to obtain Compound 14 (135 mg, yield 89.8%) in solid form. Step 5) 6-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)-2H-benzo[b][1,4]oxazine-3(4H)-one trifluoroacetate TFA (0.1 mL) was added to a solution of Compound 14 (5.5 mg) in DCM (0.1 mL) at room temperature and stirred for 1 hour. After the reaction was complete, the mixture was purified by reverse-phase chromatography [a gradient elution condition of high-performance liquid chromatography (HPLC), in which a solvent mixed with water (containing 0.1% formic acid (FA)) and acetonitrile (containing 0.1% FA) in an 80:20 ratio was initially used, and the ratio of acetonitrile (containing 0.1% FA) increased to 100% over time] to obtain Example 42 (3.5 mg, yield 66.4%) in solid form. 1H NMR (400 MHz, DMSO-d6)δ 10.9 (s, 1H), 8.62 (s, 2H), 7.63 (d, J = 2.0 Hz, 1H), 7.56 (dd, J = 3.0, 5.0 Hz, 1H), 7.36 (dd, J = 1.2, 2.8 Hz, 1H), 7.03-6.99 (m, 3H), 6.97-6.94 (m, 1H), 6.39 (d, J = 2.0 Hz, 1H), 4.70 (s, 2H), 3.99 (s, 2H), 2.55 (t, J = 3.9 Hz, 3H), [M+1]=404.18. Examples 43-45 Compounds of Examples 43-45 were prepared as described in Table 3 below by using the synthesis method of Example 42, utilizing compound 9 of Step 1 as an intermediate, and changing the reactant to a substance similar to compound 10. Example Number Chemical Structure / Chemical Name NMR Data Molecular Weight [M+1] 42 6-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)-2H-benzo[b][1,4]oxazine-3(4H)-one trifluoroacetate 1 H NMR (400 MHz, DMSO-d6) δ 8.22 (s, 1H), 7.53 (dd, J = 5.0, 3.0 Hz, 1H), 7.40 (s, 1H), 7.35 (dd, J = 2.8, 1.2 Hz, 1H), 7.02-6.98 (m, 3H), 6.95-6.92 (dd, J = 8.6, 2.2 Hz, 1H), 6.32 (d, J = 2.0 Hz, 1H), 4.68 (s, 2H), 3.65 (s, 2H), 2.36 (s, 3H)404.1843 6-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)-2H-benzo[b][1,4]oxazine-3(4H)-one trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 10.94 (s, 1H), 8.62 (s, 1H), 7.67 (d, J = 1.6 Hz, 1H), 7.55-7.52 (m, 1H), 7.50-7.49 (m, 2H), 7.25-6.95 (m, 4H), 6.42 (s, 1H), 4.72 (s, 2H), 4.02 (s, 2H), 2.56 (t, J = 3.9 Hz, 3H))416.0544 6-((2-(2,4-difluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)-2H-benzo[b][1,4]oxazine-3(4H)-one trifluoroacetate 1 H NMR (400 MHz, DMSO-d6) δ 10.90 (s, 1H), 8.56 (s, 2H), 7.62 (d, J = 1.6 Hz, 1H), 7.47-7.40 (m, 1H), 7.06-6.99 (m, 4H), 6.84 (d, J = 2.0) Hz, 1H), 6.37 (d, J = 2.0 Hz, 1H, 4.66 (s, 2H), 3.93 (s, 2H), 2.49 (t, J = 3.9 Hz, 3H)434.3045 7-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)-2H-benzo[b][1,4]oxazine-3(4H)-one trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 11.17 (s, 1H), 8.67-8.55 (bs, 2H), 7.65 (d, J = 1.6 Hz, 1H), 7.57 (dd, J = 3.0, 5.0 Hz, 1H), 7.37 (dd, J = 1.2, 2.8 Hz, 1H), 7.04 (dd, J = 2.2, 8.2 Hz, 1H), 7.01 (dd, J = 1.4, 5.0 Hz, 1H), 6.92 (d, J = 8.4 Hz, 1H), 6.84 (d, J = 2.0 Hz, 1H), 6.39 (d, J = 2.0 Hz, 1H), 4.65 (s, 2H), 3.99 (t, J = 5.2 Hz, 2H), 2.55 (t, J = 5.0 Hz, 3H)404.14 Synthesis Method 4 Example 46 1-(1-((3,4-dihydro-2H-benzo[b][1,4]oxazine-6-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate Step 1) tert-butyl ((1-((4-(2-chloroethoxy)-3-nitrophenyl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)methyl)(methyl)carbamate Compound 11 (50 mg, 0.1 mmol, 1.0 equivalent) was dissolved in DMF (2 mL), and then K2CO3 (42 mg, 0.3 mmol, 3.0 equivalent) and 1-chloro-2-iodoethane (91.9 μL, 1.01 mmol, 10.0 equivalent) were added at room temperature. The reaction mixture was heated to 80°C to complete the reaction, after which water was added and extracted twice with CH2Cl2, the organic layer was dried with Na2SO4, and then concentrated under reduced pressure. After the reaction was complete, the mixture was purified by reverse-phase chromatography [high-performance liquid chromatography (HPLC) gradient elution conditions, in which a solvent mixed with water (containing 0.1% formic acid (FA)) and acetonitrile (containing 0.1% FA) in an 80:20 ratio was initially used, and the ratio of acetonitrile (containing 0.1% FA) increased to 100% over time] to obtain compound 16 (83 mg, yield 82.7%) in solid form. 1 H NMR (400 MHz, DMSO-d6)δ 7.81 (d, J = 2.4 Hz, 1H), 7.64 (dd, J = 8.8, 2.4 Hz, 1H), 7.55 (dd, J = 4.8, 2.8 Hz, 1H), 7.51 (d, J = 8.8 Hz, 1H), 7.42 (d, J = 2.0 Hz, 1H), 7.40 (d, J = 2.0 Hz, 1H), 7.06 (dd, J = 4.8, 1.2 Hz, 1H), 6.23 (s, 1H), 4.53 (t, J = 5.2, 5.2 Hz, 2H), 4.16 (s, 2H), 3.95 (t, J = 5.2, 4.8 Hz, 2H), 2.74 (s, 3H), 1.39 (s, 9H), [M+1]=566.16. Step 2) tert-butyl ((1-((3-amino-4-(2-chloroethoxy)phenyl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)methyl)(methyl)carbamate Compound 16 (80 mg, 1.0 equivalent) was dissolved in DMSO (1 mL), to which B2(OH)4 (38.6 mg) and 4,4-bipyridine (1.9 mg, 5 mol%) were added and stirred at room temperature. After the reaction was complete, the mixture was purified by reverse-phase chromatography [high-performance liquid chromatography (HPLC) gradient elution conditions, in which a solvent mixture of water (containing 0.1% formic acid (FA)) and acetonitrile (containing 0.1% FA) in an 80:20 ratio was initially used, and the proportion of acetonitrile (containing 0.1% FA) increased to 100% over time] to obtain Compound 17 (57 mg, yield 76.1%) in solid form. 1 H NMR (400 MHz, DMSO-d6)δ 7.50 (dd, J = 4.8, 3.2 Hz, 1H), 7.39 (d, J = 1.2 Hz, 1H), 7.26 (d, J = 1.6 Hz, 1H), 7.04 (d, J = 5.2 Hz, 1H), 6.84 (d, J = 8.4 Hz, 1H), 6.79 (d, J = 2.4 Hz, 1H), 6.55 (dd, J = 8.4, 2.4 Hz, 1H), 6.19 (s, 1H), 5.20 (d, J = 7.6 Hz, 1H), 4.27 (t, J = 4.8, 5.6 Hz, 2H), 4.16 (s, 2H), 3.94 (t, J = 5.2, 5.2 Hz, 2H), 2.74 (s, 3H), 1.40 (s, 9H), [M+1]=526.24. Step 3) tert-butyl ((1-((3-((tert-butoxycarbonyl)amino)-4-(2-chloroethoxy)phenyl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)methyl)(methyl)carbamate Compound 17 (49 mg, 1.0 equivalent) was dissolved in DMF (0.5 mL), and then DIPEA (32.6 µL) was added. Subsequently, BoC2O (43.1 µL) was added to the reaction solution, and the reaction was completed by heating to 80°C. After the reaction was complete, water was added and extracted twice with CH2Cl2, the organic layer was dried with Na2SO4, and then concentrated under reduced pressure. After the reaction was complete, the mixture was purified by reverse-phase chromatography [high-performance liquid chromatography (HPLC) gradient elution conditions, in which a solvent mixture of water (containing 0.1% formic acid (FA)) and acetonitrile (containing 0.1% FA) in an 80:20 ratio was initially used, and the proportion of acetonitrile (containing 0.1% FA) increased to 100% over time] to obtain Compound 18 (45 mg, yield 77.2%) in solid form. 1 H NMR (400 MHz, DMSO-d6)δ 8.16 (s, 1H), 7.99 (bs, 1H), 7.50 (dd, J = 4.8, 2.8 Hz, 1H), 7.38 (s, 1H), 7.30 (d, J = 1.6 Hz, 1H), 7.11 (d, J = 8.80 Hz, 1H), 7.05-7.02 (m, 2H), 6.18 (s, 1H), 4.35 (t, J = 5.2, 5.6 Hz, 2H), 4.16 (s, 2H), 4.01 (t, J = 5.2, 5.2 Hz, 2H), 2.73 (s, 3H), 1.48 (s, 9H), 1.39 (s, 9H), [M+1]=626.36. Step 4) tert-butyl 6-((4-(((tert-butoxycarbonyl)(methyl)amino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)-2,3-dihydro-4H-benzo[b][1,4]oxazine-4-carboxylate Compound 18 (43 mg) was dissolved in a 0.3 mL DMF solution and cooled to 0°C. NaH (60% in oil, 6 mg) was added, and the reaction was completed by stirring at room temperature for 1 hour. After the reaction was complete, water was added and extracted twice with CH2Cl2, the organic layer was dried with Na2SO4, and then concentrated under reduced pressure. After the reaction was complete, the mixture was purified by reverse-phase chromatography [high-performance liquid chromatography (HPLC) gradient elution conditions, in which a solvent mixture of water (containing 0.1% formic acid (FA)) and acetonitrile (containing 0.1% FA) in an 80:20 ratio is initially used, and the proportion of acetonitrile (containing 0.1% FA) increases to 100% over time] to obtain Compound 19 (22 mg, yield 45.9%) in solid form. 1 H NMR (400 MHz, DMSO-d6)δ 7.95 (s, 1H), 7.50 (dd, J = 5.0, 3.0 Hz, 1H), 7.38 (d, J = 2.0 Hz, 1H), 7.29 (d, J = 1.6 Hz, 1H), 7.03 (dd, J = 5.0, 1.0 Hz, 1H), 6.98 (dd, J = 8.8, 2.0 Hz, 1H), 6.92 (d, J = 8.8 Hz, 1H), 6.18 (s, 1H), 4.27 (t, J = 4.0, 4.8 Hz, 2H), 4.15 (s, 2H), 3.78 (t. J = 4.4, 4.4 Hz, 2H), 2.74 (s, 3H), 1.47 (s, 9H), 1.39 (s, 9H), [M+1]=590.37. Step 5) 1-(1-((3,4-dihydro-2H-benzo[b][1,4]oxazine-6-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate TFA (0.25 mL) was added to a solution of Compound 19 (20 mg) in CH2Cl2 (0.25 mL) at room temperature and stirred for 1 hour. After the reaction was complete, the mixture was purified by reverse-phase chromatography [a gradient elution condition of high-performance liquid chromatography (HPLC), in which a solvent mixed with water (containing 0.1% formic acid (FA)) and acetonitrile (containing 0.1% FA) in an 80:20 ratio was initially used, and the ratio of acetonitrile (containing 0.1% FA) increased to 100% over time] to obtain Example 46 (11.8 mg, yield 68.1%) in solid form. 1 H NMR (400 MHz, DMSO-d6)δ 8.59 (bs, 2H), 7.57 (d, J = 1.6 Hz, 1H), 7.54 (dd, J = 5.0, 3.0 Hz, 1H), 7.38 (dd, J = 3.0, 1.4 Hz, 1H), 7.01 (dd, J = 4.8, 1.2 Hz, 1H), 6.71 (d, J = 2.4 Hz, 1H), 6.68 (d, J = 8.4 Hz, 1H), 6.50 (dd, J = 8.8, 2.4 Hz, 1H), 6.38 (d, J = 2.0 Hz, 1H), 4.16 (t, J = 4.0, 4.4 Hz, 2H), 4.01-3.96 (m, 2H), 3.26 (t, J = 4.4, 4.0 Hz, 2H), 2.54 (dd, J = 5.20, 2.06 Hz, 3H), [M+1]=390.15. Examples 47~49 Compounds of Examples 47-49 were prepared as described in Table 4 below by using the synthesis method of Example 46, utilizing compound 16 of Step 1 as an intermediate, and changing the reactant to a substance similar to compound 15. Example Number Chemical Structure / Name NMR Data Molecular Weight [M+1] 46 1-(1-((3,4-dihydro-2H-benzo[b][1,4]oxazine-6-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1 H NMR (400 MHz, DMSO-d6) δ 8.59 (bs, 2H), 7.57 (d, J = 1.6 Hz, 1H), 7.54 (dd, J = 5.0, 3.0 Hz, 1H), 7.38 (dd, J = 3.0, 1.4 Hz, 1H), 7.01 (dd, J = 4.8, 1.2 Hz, 1H), 6.71 (d, J = 2.4 Hz, 1H), 6.68 (d, J = 8.4 Hz, 1H), 6.50 (dd, J = 8.8, 2.4 Hz, 1H), 6.38 (d, J = 2.0 Hz, 1H), 4.16 (t, J = 4.0, 4.4 Hz, 2H), 4.01-3.96 (m, 2H), 3.26 (t, J = 4.4, 4.0 Hz, 2H), 2.54 (dd, J = 5.20, 2.06 Hz, 3H)390.1547 N-methyl-1-(1-((2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine-7-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)methaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.64-8.52 (bs, 2H), 7.59 (d, J = 2.0 Hz, 1H), 7.54 (dd, J = 5.0, 3.0 Hz, 1H), 7.35 (dd, J = 3.2, 1.2 Hz, 1H), 6.98 (dd, J = 5.0, 1.2 Hz, 1H), 6.96 (d, J = 2.4 Hz, 1H), 6.81 (d, J = 8.4 Hz, 1H), 6.59 (dd, J = 8.4, 2.4 Hz, 1H), 6.39 (d, J = 2.0 Hz, 1H), 4.09 (t, J = 5.6, 5.6 Hz, 2H), 3.99 (t, J =5.6, 5.2 Hz, 2H), 3.13 (t, J = 6.0, 5.6 1H), 2.55 (t, J = 5.2, 5.2 Hz, 1H), 1.92-1.84 (m, 2H)403.3748 1-(1-((3,4-dihydro-2H-benzo[b][1,4]oxazine-7-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate 1 H NMR (400 MHz, DMSO-d6) δ 8.67-8.48 (bs, 2H), 7.57-7.54 (m, 2H), 7.37 (dd, J = 1.2, 2.8 Hz, 1H), 7.09 (s, 1H), 7.03 (dd, J = 1.2, 4.8 Hz, 1H), 6.75 (dd, J = 2.2, 8.6 Hz, 1H), 6.60 (d, J = 2.4 Hz, 1H), 6.48 (d, J = 8.8 Hz, 1H), 6.34 (d, J = 2.0 Hz, 1H), 4.06 (t, J = 4.4 Hz, 2H), 3.97 (s, 2H), 2.55 (t, J = 3.6 Hz, 3H)390.1549 N-methyl-1-(1-((2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine-8-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)methaneamine trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 8.67-8.48 (bs, 2H), 7.58 (d, J = 1.6 Hz, 1H), 7.56 (dd, J = 2.8, 4.8 Hz, 1H), 7.37 (dd, J = 1.2, 2.8 Hz, 1H), 7.02 (dd, J = 1.2, 4.8 Hz, 1H), 6.83 (dd, J = 2.2, 4.6 Hz, 1H), 6.67-6.62 (m, 2H), 6.55 (t, J = 3.8 Hz, 1H), 6.35 (d, J = 2.0 Hz, 1H), 4.06 (t, J = 6.0 Hz, 2H), 3.98 (s, 2H), 2.55 (s, 3H), 1.95-1.89 (m, 2H)404.22 Synthesis Method 5 Example 50 5-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate Step 1) tert-butyl ((5-(2-fluorophenyl)-1-((4-hydroxy-3-nitrophenyl)sulfonyl)-1H-pyrrole-3-yl)methyl)(methyl)carbamate Compound 20 (299 mg) was dissolved in a DMF (5.0 mL) solution, and NaH (60% in oil, 118 mg) was added at 0°C. After stirring for 30 minutes at the same temperature, 4-hydroxy-3-nitrobenzenesulfonyl chloride (468 mg) was slowly added over 5 minutes. Then, the reaction was completed by stirring at room temperature for 1 hour. After terminating the reaction by adding water to the reaction mixture, the mixture was extracted twice with CH2Cl2, dried with Na2SO4, and concentrated under reduced pressure. After the reaction was complete, the mixture was purified by reverse-phase chromatography [high-performance liquid chromatography (HPLC) gradient elution conditions, in which a solvent mixed with water (containing 0.1% formic acid (FA)) and acetonitrile (containing 0.1% FA) in an 80:20 ratio was initially used, and the ratio of acetonitrile (containing 0.1% FA) increased to 100% over time] to obtain compound 21 (403 mg, yield 81.1%) in the form of a pale yellow solid. 1 H NMR (400 MHz, DMSO-d6)δ 7.75 (d, J = 2.4 Hz, 1H), 7.58 (dd, J = 9.0, 2.6 Hz, 1H), 7.52-7.45 (m, 1H), 7.42 (d, J = 1.6 Hz, 1H), 7.22-7.14 (m, 4H), 6.26 (s, 1H), 4.17 (s, 2H), 2.74 (s, 3H), 1.37 (s, 9H), [M+1]=506.50. Step 2) tert-butyl ((1-((3-amino-4-hydroxyphenyl)sulfonyl)-5-(2-fluorophenyl)-1H-pyrrole-3-yl)methyl)(methyl)carbamate To a solution in which Compound 21 (399 mg, 1.0 equivalent) was dissolved in DMSO (5 mL), B2(OH)4 (193 mg) and 4,4-bipyridine (10 mg, 5 mol%) were added and stirred at room temperature. After the reaction was complete, the mixture was purified by reverse-phase chromatography [high-performance liquid chromatography (HPLC) gradient elution conditions, in which a solvent mixture of water (containing 0.1% formic acid (FA)) and acetonitrile (containing 0.1% FA) in an 80:20 ratio was initially used, and the proportion of acetonitrile (containing 0.1% FA) increased to 100% over time] to obtain Compound 22 (82 mg, yield 21.8%) in solid form. 1 H NMR (400 MHz, DMSO-d6)δ 7.49-7.43 (m, 1H), 7.25 (d, J = 2.0 Hz, 1H), 7.21-7.10 (m, 3H), 6.71 (d, J = 2.4 Hz, 1H), 6.62 (d, J = 8.4 Hz, 1H), 6.45 (dd, J = 8.4, 2.4 Hz, 1H), 6.17 (s, 1H), 4.17 (s, 2H), 2.73 (s, 3H), 1.38 (s, 9H), [M+1]=476.52. Step 3) tert-butyl ((5-(2-fluorophenyl)-1-((2-oxo-2,3-dihydrobenzo[d]oxazole-5-yl)sulfonyl)-1H-pyrrole-3-yl)methyl)(methyl)carbamate 1,1'-carbonyldiimidazole (CDI, 56 mg) was added to a solution of compound 22 (82 mg) dissolved in DMF (1 mL) and stirred at room temperature for 10 minutes. After the reaction was complete, water was added to the reaction mixture to terminate the reaction. Subsequently, the mixture was extracted twice with CH2Cl2, dried with Na2SO4, and concentrated under reduced pressure. After the reaction was complete, the mixture was purified by reverse-phase chromatography [high-performance liquid chromatography (HPLC) gradient elution conditions, in which a solvent mixture of water (containing 0.1% formic acid (FA)) and acetonitrile (containing 0.1% FA) in an 80:20 ratio was initially used, and the proportion of acetonitrile (containing 0.1% FA) increased to 100% over time] to obtain compound 24 (73 mg, yield 84.8%) in solid form. 1 H NMR (400 MHz, DMSO-d6)δ 12.07 (s, 1H), 7.53-7.47 (m, 1H), 7.45-7.40 (m, 2H), 7.25-7.17 (m, 3H), 7.12 (dt, J = 7.2, 7.4, 1.3 Hz, 1H), 6.98 (d, J = 2.0 Hz, 1H), 6.23 (s, 1H), 4.17 (s, 3H), 2.74 (s, 3H), 1.34 (s, 9H)), [M+1]=502.51. Step 4) 5-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate TFA (1 mL) was added to a solution of Compound 24 (82 mg) in CH2Cl2 (1 mL) at room temperature and stirred for 1 hour. After the reaction was complete, the mixture was purified by reverse-phase chromatography [a gradient elution condition of high-performance liquid chromatography (HPLC), in which a solvent mixed with water (containing 0.1% formic acid (FA)) and acetonitrile (containing 0.1% FA) in an 80:20 ratio was initially used, and the ratio of acetonitrile (containing 0.1% FA) increased to 100% over time] to obtain Example 50 (41 mg, yield 49.4%) in solid form. 1 H NMR (400 MHz, DMSO-d6)δ 12.14 (s, 1H), 8.73-8.52 (bs, 2H), 7.75 (d, J = 1.6 Hz, 1H), 7.57-7.51 (m, 1H), 7.46 (d, J = 8.4 Hz, 1H), 7.26-7.19 (m, 3H), 7.07 (td, J = 7.6, 7.4, 1.7 Hz, 1H), 6.97 (d, J = 1.6 Hz, 1H), 6.43 (d, J = 2.0 Hz, 1H), 4.02-3.98 (m, 2H), 2.57-2.53 (m, 3H), [M+1]=402.41. Example 51 Compound of Example 51 was prepared as described in Table 5 below by using the synthesis method of Example 50 and varying the reactant to a substance similar to compound 20. Example Number Chemical Structure / Name NMR Data Molecular Weight [M+1] 50 5-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate 1H NMR (400 MHz, DMSO-d6) δ 12.14 (s, 1H), 8.73-8.52 (bs, 2H), 7.75 (d, J = 1.6 Hz, 1H), 7.57-7.51 (m, 1H), 7.46 (d, J = 8.4 Hz, 1H), 7.26-7.19 (m, 3H), 7.07 (td, J = 7.6, 7.4, 1.7 Hz, 1H), 6.97 (d, J = 1.6 Hz, 1H), 6.43 (d, J = 2.0 Hz, 1H), 4.02-3.98 (m, 2H), 2.57-2.53 (m, 3H)402.4151 5-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate 1 H NMR (400 MHz, DMSO-d6) δ 12.16 (br, 1H), 8.66 (br, 2H), 7.69 (d, J = 1.6 Hz, 1H), 7.56 (dd, J = 5.0, 3.0 Hz, 1H), 7.41 (d, J = 8.4 Hz, 1H), 7.33 (dd, J = 2.8, 1.2 Hz, 1H), 7.19 (dd, J = 8.4, 2.0 Hz, 1H), 6.99 (dd, J = 5.2, 1.2 Hz, 1H), 6.95 (d, J = 2.0 Hz, 1H), 6.39 (d, J = 2.0 Hz, 1H), 3.98 (s, 2H), 2.54 (s, 3H)390.30 Experimental Example 1: Preparation of gastric vesicles The gastrointestinal vesicles used in the experiment were prepared by isolating them from the porcine gastric mucosa using the centrifugation method [Saccomani G, et al., A Nonelectrogenic H Pump in Plasma Membranes of Hog Stomach, J Biol Chem., 1976, 251(23), 7690~8]. Subsequently, the protein contents of the gastrointestinal vesicles were quantified using a bicinchoninic acid kit [Smith PK, et al., Measurement of protein using bicinchoninic acid, Anal Biochem., 1985, 150(1), 76~85)]. Experimental Example 2: Measurement of Inhibitory Effect on Proton Pump (H+ / K+-ATPase) Activity The inhibitory activity of the compounds of Examples 1 to 48 on proton pump (H+ / K+-ATPase) activity was measured as follows. Gastric vesicles are obtained from a pig's stomach by a known method (

[0427] It was prepared according to Edd C. Rabon et al., Preparation of Gastric H+,K+-ATPase., Methods in enzymology, vol.157 Academic Press Inc., (1988), pp.649-654). The protein contents of the prepared gastrointestinal vesicles were quantified using a Bicinchoninic Acid (BCA) kit (Thermo). 80 µl of (test compound at a specified concentration, 3 mM MgSO4, 6 mM KCl, 60 mM Tris-HCl, pH 6.4) was added to each well of a 96-well plate. To each well, 10 µl of reaction solution containing gastrointestinal vesicles (60 mM, Tris-HCl, pH 6.4) and 10 µl of Tris buffer solution containing adenosine triphosphate (1 mM ATP, 60 mM Tris-HCl, pH 6.4) were added, and the enzymatic reaction was carried out at 37°C for 60 minutes. The enzymatic reaction was stopped by adding 25 µl of malachite green solution (Sigma-Aldrich). The amount of monophosphate (Pi) in the reaction solution was measured at 600 nm using a microplate reader (GloMax® Discover Microplate Reader, Promega). The inhibition rate (%) was measured from the activity value of the highest concentration of the test compound and the activity values ​​of various concentrations of the test compound, and the concentration that inhibits H+ / K+-ATPase activity by 50% (IC10) 50 ) was calculated from each % inhibition value of the compound using the GraphPad Prism 8 program. The results are shown in Table 6 below. Example IC 50 Example IC 50 1+++27+++2+++28+++3+++29++4+++30+++5+++31+6+++32++7+++33+++8++34+++9++35++10++36++11++37++12++38++13++39+++14++40+++15+++41+++16++42++17+43+++18+++44++19+++45++20+++46++21+++47++22+++48+++23+++49++24++50+++25+++51+++26++ * IC 50 If the value is less than 50 nM: +++ * IC 50 If the value is 50~500 nM: ++ * IC 50 If the value exceeds 500 nM: + Experimental Example 3: Inhibitory effect on histamine-stimulated gastric acid secretion in pylorus-ligated rats The inhibitory effect of the compound of the present invention on histamine-stimulated gastric acid secretion was performed by applying the Shay's rat model [Shay H, et al., A simple method for the uniform production of gastric ulceration in the rat, Gastroenterology, 1945, 5, 43~61]. Male Sprague Dawley (SD) rats (body weight 180–210 g) were divided into group X (n=7) and fasted for 24 hours with only water. Thirty minutes prior to pyloric ligation, the control group was orally administered only a 5% DMSO, 95% 0.5% methylcellulose (MC) aqueous solution, while the other groups were orally administered the test compound at a dose of 3 mg / kg in a 5% DMSO, 95% 0.5% methylcellulose (MC) aqueous solution. Under isoflurane anesthesia, the peritoneum of the rats was incised and the pylorus was ligated. Immediately after ligation, histamine (Histamine 2HCl) was administered subcutaneously at a dose of 7.5 mg / 2.5 ml / head. Four hours after ligation, the test animals were euthanized and the stomachs were excised. The contents obtained were centrifuged at 4,000 rpm for 10 minutes to separate only the supernatant, thereby obtaining gastric juice. Subsequently, the volume (ml) of 0.01 N-NaOH required for automatic titration of gastric acid to pH 7.0 was measured. The total acidity (total acid output) was calculated according to Equation 1 below by multiplying the concentration of NaOH (0.01) by the total volume of gastric juice and dividing by the volume of gastric juice used for titration. [Equation 1] Total acidity (μEq) = (0.01N NaOH (ml) × 0.01 × Total gastric fluid volume (ml) × 1,000) / (0.2 (Volume of gastric fluid used for titration)) % inhibition ability was calculated according to Equation 2 below, and the results are shown in Table 7. [Equation 2] % inhibitory activity of example compound = 100 - (100 × total acidity of example compound / average total acidity of control group) Compound Gastric Acid Secretion Inhibitory Activity (%, 3 mg / kg) Vehicle / Control 0 Example 1 100 Example 6 92.08 Example 9 90.30 Example 15 100 Example 3 071.09 Example 3 354.40 Example 3 465.91 Example 3 756.40 Example 4 856.75 As shown in Table 7, the compounds of the present invention have excellent inhibitory activity against histamine-stimulated gastric acid secretion in pyloric-ligated rats.

Claims

1. A compound represented by the following chemical formula I or a pharmaceutically acceptable salt thereof: [Chemical Formula I] In chemical formula I, is a heterobicyclic ring, and R1 is a phenyl, or a 5- or 6-membered hetero ring, and R2 is H, or a C1-C3 alkoxy, and R3 is H, or C1-C4 alkyl, and R4 is H, or C1-C4 alkyl.

2. In Paragraph 1, Is , , , , , , , , , , , , , , , , , , , , , , and A compound represented by the above formula I or a pharmaceutically acceptable salt thereof, selected from the group consisting of 3. In Paragraph 1, R1 is , , , , , , , , , , , , , , , , , , , , , , , and A compound represented by the above formula I or a pharmaceutically acceptable salt thereof, selected from the group consisting of 4. In Paragraph 1, A compound represented by the above formula I or a pharmaceutically acceptable salt thereof, wherein R2 and R3 are each independently H.

5. In Paragraph 1, A compound represented by the above formula I or a pharmaceutically acceptable salt thereof, wherein R4 is methyl.

6. In Paragraph 1, 1-(1-(benzofuran-5-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(5-methylthiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(4-methylthiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(2-methylthiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-4-(2,5-dimethylthiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 4-(1-(benzofuran-5-yl-sulfonyl)-4-((methylamino)methyl)-1H-pyrrole-2-yl)thiophene-2-carbonitrile trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(2-chlorothiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(isothiazole-4-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(furan-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(2,5-dimethylfuran-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(1H-pyrazole-4-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(1-methyl-1H-pyrazole-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; Ethyl 2-(4-(1-(benzofuran-5-yl-sulfonyl)-4-((methylamino)methyl)-1H-pyrrole-2-yl)-1H-pyrazole-1-yl)acetate trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(furan-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(thiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(4-(1-(benzofuran-5-yl-sulfonyl)-4-((methylamino)methyl)-1H-pyrrole-2-yl)thiophene-2-yl)ethane-1-one trifluoroacetate; 4-(1-(benzofuran-5-yl-sulfonyl)-4-((methylamino)methyl)-1H-pyrrole-2-yl)thiophene-2-carboxamide trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(5-fluorothiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(3-methylthiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(5-methylthiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(4-methylthiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-7-yl-sulfonyl)-5-(thiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; N-methyl-1-(1-(thieno[3,2-b]pyridine-6-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)methaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(thiazole-5-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-6-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(5-(trifluoromethyl)thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzo[b]thiophene-6-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzo[d]thiazole-6-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-((2,2-difluorobenzo[d][1,3]dioxol-4-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 6-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]thiazole-2(3H)-one trifluoroacetate; 3-methyl-6-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]thiazole-2(3H)-one trifluoroacetate; 6-((2-(isothiazole-4-yl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]thiazole-2(3H)-one trifluoroacetate; 3-methyl-5-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate; 1-(1-((2,3-dihydrobenzofuran-5-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 3,3-dimethyl-5-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)indolin-2-one trifluoroacetate; 1,3-dimethyl-5-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)-1,3-dihydro-2H-benzo[d]imidazole-2-one trifluoroacetate; 6-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]thiazole-2(3H)-one trifluoroacetate; 6-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate; 1-(1-(benzo[d][1,3]dioxol-5-ylsulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(indolin-5-ylsulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-((2,3-dihydro-1H-indene-5-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 6-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)-2H-benzo[b][1,4]oxazine-3(4H)-one trifluoroacetate; 6-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)-2H-benzo[b][1,4]oxazine-3(4H)-one trifluoroacetate; 6-((2-(2,4-difluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)-2H-benzo[b][1,4]oxazine-3(4H)-one trifluoroacetate; 7-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)-2H-benzo[b][1,4]oxazine-3(4H)-one trifluoroacetate; 1-(1-((3,4-dihydro-2H-benzo[b][1,4]oxazine-6-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; N-methyl-1-(1-((2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine-7-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)methaneamine trifluoroacetate; 1-(1-((3,4-dihydro-2H-benzo[b][1,4]oxazine-7-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; N-methyl-1-(1-((2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine-8-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)methaneamine trifluoroacetate; 5-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate; and A compound represented by the formula I or a pharmaceutically acceptable salt thereof, selected from the group consisting of 5-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate.

7. In Paragraph 6, 1-(1-(benzofuran-5-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(5-methylthiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(4-methylthiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(2-methylthiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-4-(2,5-dimethylthiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 4-(1-(benzofuran-5-yl-sulfonyl)-4-((methylamino)methyl)-1H-pyrrole-2-yl)thiophene-2-carbonitrile trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(2-chlorothiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(furan-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(thiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(5-fluorothiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(3-methylthiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(5-methylthiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-5-yl-sulfonyl)-5-(4-methylthiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzofuran-7-yl-sulfonyl)-5-(thiophene-2-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; N-methyl-1-(1-(thieno[3,2-b]pyridine-6-ylsulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)methaneamine trifluoroacetate; 1-(1-(benzofuran-6-ylsulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzo[b]thiophene-6-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(benzo[d]thiazole-6-yl-sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 6-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]thiazole-2(3H)-one trifluoroacetate; 3-methyl-5-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate; 1-(1-((2,3-dihydrobenzofuran-5-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 6-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate; 1-(1-(benzo[d][1,3]dioxol-5-ylsulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-(indolin-5-ylsulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 1-(1-((2,3-dihydro-1H-indene-5-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 6-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)-2H-benzo[b][1,4]oxazine-3(4H)-one trifluoroacetate; 1-(1-((3,4-dihydro-2H-benzo[b][1,4]oxazine-7-yl)sulfonyl)-5-(thiophene-3-yl)-1H-pyrrole-3-yl)-N-methylmethaneamine trifluoroacetate; 5-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate; and A compound represented by the formula I or a pharmaceutically acceptable salt thereof, selected from the group consisting of 5-((4-((methylamino)methyl)-2-(thiophene-3-yl)-1H-pyrrole-1-yl)sulfonyl)benzo[d]oxazole-2(3H)-one trifluoroacetate.

8. A pharmaceutical composition for inhibiting potassium-competitive gastric acid secretion comprising, as an active ingredient, a compound represented by the chemical formula I of any one of claims 1 to 7 or a pharmaceutically acceptable salt thereof.

9. In Paragraph 8, A pharmaceutical composition for inhibiting potassium-competitive gastric acid secretion, further comprising a pharmaceutically acceptable carrier, diluent, or excipient.

10. A pharmaceutical composition for the prevention or treatment of a disease caused by gastric acid secretion disorder, comprising as an active ingredient a compound represented by the chemical formula I of any one of claims 1 to 7 or a pharmaceutically acceptable salt thereof.

11. In Paragraph 10, A pharmaceutical composition for the prevention or treatment of a disease caused by gastric acid secretion disorder, wherein the disease caused by the above gastric acid secretion disorder is selected from the group consisting of gastrointestinal disease, gastroesophageal disease, gastroesophageal reflux disease (GERD), peptic ulcer, gastric ulcer, duodenal ulcer, NSAID-induced ulcer, gastritis, Helicobacter pylori infection, dyspepsia, functional dyspepsia, Zollinger-Ellison syndrome, non-erosive reflux disease (NERD), visceral referred pain, heartburn, nausea, esophagitis, dysphagia, drooling, airway obstruction, and asthma.

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