Therapeutic agents for irritable bowel syndrome
A technology for irritable bowel syndrome and therapeutic agent, which can be applied in the fields of drug combination, active ingredients of heterocyclic compounds, organic chemistry, etc., can solve the problems such as the limitation of treatment options for IBS
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
reference example 1
[0280] Reference Example 1: 5,5-dioxo-9-(2-ethyl-2-hydroxybutyrylamino)-4,10-dihydrothiophene And[3,2-c][1]benzothiapin-10-one (compound 1-4)
[0281] Step 1: 9-(tert-butoxycarbonylamino)-4,10-dihydrothieno[3,2-c][1]benzothiapine -10-one
[0282] To 9-amino-4,10-dihydrothieno[3,2-c][1]benzothiapin-1-one (WO98 / 46587) (20g) in tetrahydrofuran (THF) (40mL) solution Di-tert-butyl dicarbonate (35.3 g) was added and stirred under reflux for about 16 hours. Di-tert-butyl dicarbonate (17.7 g) was added again, and stirred under reflux for about 24 hours. The reaction mixture was cooled to room temperature, silica gel was added, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane / ethyl acetate=10 / 1). Hexane was added to the obtained crude crystals, stirred at room temperature, filtered, washed with hexane, and dried under reduced pressure to obtain the title compound (26.75 g).
[0283] Step 2: 9-(tert-butoxycarbonylamino)...
reference example 2
[0291] Reference Example 2: 5,5-dioxo-9-[(5-methylpyrazol-3-ylcarbonyl)amino]-4,10-dihydrothiazol Pheno[3,2-c][1]benzothiapin-10-one (compound 1-9)
[0292] Step 1: 5-Methylpyrazole-3-carboxylic acid
[0293] Methyl 5-methylpyrazole-3-carboxylate (1.00 g, 6.49 mmol) was dissolved in methanol (6.5 mL), and 3.5 mol / L aqueous sodium hydroxide solution (6.5 mL) was added at room temperature, followed by stirring for 1.5 hours. Water was added to the reaction mixture, washed with ether, adjusted to pH 1 by adding 1 mol / L hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained white crystals were washed with diethyl ether to obtain the title compound (0.25 g, 31%).
[0294] Step 2: 9-[(5-methylpyrazol-3-ylcarbonyl)amino]-4,10-dihydrothieno[3,2-c][1] Benzothiapin-10-one
[0295] The 5-methylpyrazole-3-carboxylic acid (0.1...
Embodiment 1
[0304] 5,5-dioxo-9-phenylamino-4,10-dihydrothieno[3,2-c][1]benzothiapin-10-one (compound 5-1)
[0305] Step 1: 9-Phenylamino-4,10-dihydrothieno[3,2-c][1]benzothiapin-10-one
[0306] 9-Amino-4,10-dihydrothieno[3,2-c][1]benzothiapin-10-one (WO98 / 46587) (200mg, 0.81mmol) and phenylboronic acid (0.4g , 3.3mmol) were dissolved in dichloromethane (5mL), copper acetate (0.44g, 2.4mmol) and triethylamine (0.5mL) were added, and stirred overnight at room temperature. Copper acetate (0.29 g, 1.6 mmol) and triethylamine (0.23 mL) were added again, and the mixture was stirred at room temperature for 4.5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate / hexane=1 / 4) to obtain the title compound (236 mg, 90%).
[0307] Step 2: Compound 5-1
[0308] Using the 9-phenylamino-4,10-dihydrothieno[3,2-c][1]benzothiapin-10-one obtained in step 1, compound 5 was obtained according to step 3 of re...
PUM
| Property | Measurement | Unit |
|---|---|---|
| Diameter | aaaaa | aaaaa |
Abstract
Description
Claims
Application Information
Login to View More