Inhibitors of copper-containing amine oxidases
A technology of amine oxidase and compounds, applied in the field of enzyme inhibitors, can solve problems such as not showing activity
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0116] Example 1 (1R, 2S)-2-(1-methylhydrazino)-1-phenyl-1-hydrogen maleate (1)
[0117] In an ice bath with vigorous stirring, to a suspension of (1R,2S)-2-methylamino-1-phenyl-1-propanol hydrochloride (2.02g, 10mmol) in water (50ml) was added dropwise NaNO 2 (1.38g, 20mmol) in water (10ml), followed by the dropwise addition of AcOH (0.30g, 5mmol). The mixture was stirred at room temperature for 8 hours, then extracted with EtOAc (4 x 50ml). dry (Na 2 SO 4 ) through the combined organic phases, and evaporated under reduced pressure to obtain 1.86 g of oily product of N-nitroso derivatives, which were directly used in subsequent steps without further purification.
[0118] To the stirred LiAlH 4 (1R, 2S)-2-methylamino-N-nitroso-1-phenyl-1-propanol (1.86 g, 9.6 mmol) was added dropwise to a suspension of (0.73 g, 19.2 mmol) in THF (50 ml). ) in THF (20ml), the mixture was stirred and refluxed for 3 hours. with H 2 A mixture of O (1.5ml) and THF (20...
Embodiment 2
[0119] Embodiment 2 (1R * , 2S * )-2-(1-methylhydrazino)-1-phenyl-1-propanol hydrochloride (2)
[0120] Add (1R * , 2S * )-2-Methylamino-1-phenyl-1-propanol (0.86g, 5.3mmol) in ether (5ml). The resulting reaction mixture was stirred at room temperature for 30 minutes and evaporated to dryness. To the residue was added 5% hydrochloric acid (30ml), and the mixture was stirred at ambient temperature for 1 hour. with Et 2 O (2×30ml) washed the mixture with Na 2 CO 3 Basified and extracted with EtOAc (3 x 50ml). The combined EtOAc extracts were dried and evaporated to give a solid residue which was dissolved in methanol (5ml) and converted to the crystalline salt with 22% ethanolic hydrochloric acid (2ml) and diethyl ether salt. The crystals were filtered off and recrystallized from methanol / ether. 1 H-NMR (400MHz, D 2 O) δ (ppm): 1.20 (3H, d, J = 6.8Hz, CHCH 3 ), 3.09 (3H, s, NCH 3 ), 3.67 (1H, m, NCH), 5.41 (1H, br s, OCH), 7.47 (5H, m, C 5 h ...
Embodiment 3
[0121] Embodiment 3 (1R * , 2S * )-2-(1-methylhydrazino)-1-phenyl-1-propanol hydrochloride (2)
[0122] Add dropwise (1R * , 2S * )-2-(1-methylhydrazino)-N-nitroso-1-phenyl-1-propanol (1.94g, 10mmol, prepared according to Example 1 from (1R * , 2S * )-2-Methylamino-1-phenyl-1-propanol hydrochloride) in AcOH (18ml). The temperature of the reaction mixture was maintained at 20-25°C during the addition by external cooling. After the addition was complete, the mixture was stirred at 50 °C for 1 hour, then filtered with suction, and the zinc residue was washed with H 2 A mixture of O (15ml) and AcOH (5ml) was washed. The filtrate and washings were combined and concentrated in vacuo to about 10 mL. Under ice-cooling, the solution was basified with NaOH solution, and then washed with Et 2 O (4 x 50ml) extraction. The combined ether extracts were dried and evaporated to give a yellow oil which was dissolved in methanol (5ml) and converted to the crystal...
PUM
Login to view more Abstract
Description
Claims
Application Information
Login to view more - R&D Engineer
- R&D Manager
- IP Professional
- Industry Leading Data Capabilities
- Powerful AI technology
- Patent DNA Extraction
Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.
© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap