Anti-inflammatory drug and use thereof
A pharmacy and compound technology, applied in the field of preparing anti-inflammatory drugs and heterocyclic lactone compounds, can solve the problem of low side effects
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Embodiment 1
[0047] Compound 1: (S)-2-((3aS,7aS)-1-ethyl-7a-hydroxy-2-oxooctahydro-5H-pyrrolo[3,2-c]pyridin-5-yl)- 3,3,3-Methyl trifluoropropionate and compound 2: (S)-2-((3aR,7aR)-1-ethyl-7a-hydroxy-2-oxooctahydro-5H-pyrrolo[ Synthesis of 3,2-c]pyridin-5-yl)-3,3,3-trifluoropropionic acid methyl ester
[0048]
[0049] Synthesis of Step 1IM1:
[0050]
[0051] At room temperature, slowly drop 50 mL of anhydrous THF suspension dissolved with 4.8 g of sodium hydride into 400 mL of anhydrous THF dissolved with 40.0 g of SM1, stir at room temperature for 30 min, and slowly add dropwise of anhydrous THF solution with 47.0 g of SM2 94 mL of THF solution was stirred at room temperature for 2 h, and the reaction was monitored by TLC iodine display. After the reaction was completed, 500 mL of saturated brine was added, and the product was extracted with 1000 mL of DCM. Organic layer with Na 2 SO 4 After drying, the solvent was removed by evaporation under reduced pressure. The residue w...
Embodiment 2
[0073] Compound 7: (S)-2-((S)-1-ethyl-7a-hydroxy-2-oxo-1,2,4,6,7,7a-hexahydro-5H-pyrrolo[3, 2-c]pyridin-5-yl)-3,3,3-trifluoropropionic acid methyl ester and compound 8: (S)-2-((R)-1-ethyl-7a-hydroxy-2-oxo Synthesis of Di-1,2,4,6,7,7a-hexahydro-5H-pyrrolo[3,2-c]pyridin-5-yl)-3,3,3-trifluoropropionic acid methyl ester
[0074]
[0075] Synthesis of Step 1IM1:
[0076]
[0077] At room temperature, slowly drop 96 mL of anhydrous THF suspension dissolved with 9.6 g of sodium hydride into 800 mL of anhydrous THF dissolved with 80.0 g of SM1, stir at room temperature for 30 min, and slowly add dropwise of anhydrous THF suspension with 94.1 g of SM2 dissolved therein 188 mL of THF solution was stirred at room temperature for 2 h, and the reaction was monitored by TLC iodine display. After the reaction was completed, 1000L saturated brine was added, and the product was extracted with 2000mL DCM. Organic layer with Na 2 SO 4 After drying, the solvent was removed by evaporati...
Embodiment 3
[0104] Compound 22: (S)-2-(2-chlorophenyl)-2-((3aS,7aR)-7a-hydroxyl-2-oxohexahydrofuro[3,2-c]pyridine-5(4H )-base) Synthesis of methyl acetate
[0105]
[0106] Synthesis of Step 1IM1:
[0107]
[0108] At room temperature, slowly drop 81 mL of anhydrous THF suspension with 8.1 g of sodium hydride into 673 mL of anhydrous THF dissolved with 67.3 g of SM1, stir for 30 min, and then slowly drop into anhydrous THF solution of 84.3 g of SM2 85mL and stirred at room temperature for 12h, TLC iodine display to monitor the reaction. After the reaction was completed, 700 mL of saturated brine was added and extracted with 1500 mL of DCM. Organic layer with Na 2 SO 4 After drying, the solvent was removed by evaporation under reduced pressure. The residue was purified on a basic alumina column to obtain 23.6 g (yield 27.1%) of IM1 as a colorless oily liquid (DCM / MeOH=20 / 1 to 5 / 1). LC-MS(ESI)[M+H+] + =258.4(M+H + ) is consistent with the structure.
[0109] Synthesis of step...
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