Piperazine adenosine monophosphate activated protein kinase (AMPK) agonist and medical application thereof
A technology of pharmacy and prodrug, applied in the field of piperazine compounds
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0098] 5-(2,5-Dimethylphenoxy)-1-(1-(4-((4-fluorophenyl)sulfonyl)piperazinyl))-2,2-dimethyl-1- Pentanone (Compound 3)
[0099]
[0100] Compound I-1 (10 g, 40 mmol) was dissolved in dichloromethane (160 mL), and oxalyl chloride (6.77 mL, 80 mmol) and N,N-dimethylformamide (1 mL) were added dropwise under ice-cooling conditions. After reacting for about 5.5 hours, the solvent and unreacted oxalyl chloride were distilled off under reduced pressure to obtain acid chloride. Compound II-1 (11.175g, 60mmol) was dissolved in dichloromethane (100mL), and the above-prepared acid chloride and triethylamine (16.6mL, 120mmol) were added under ice-cooling conditions, and reacted for 12 hours. The reaction system was washed with water (100mL x 3), saturated sodium carbonate solution (100mL x 2), saturated brine (100mL x 2), dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the residue was subjected to column chromatography ( Eluent: petroleum e...
Embodiment 2
[0104] 5-(2,5-Dimethylphenoxy)-1-(1-(4-((4-chlorophenyl)sulfonyl)piperazinyl))-2,2-dimethyl-1- Pentanone (compound 1)
[0105] Compound 1 was obtained with reference to the method of Example 1: 1 H NMR (300MHz, CDCl 3 )δ7.64(d, J=8.6Hz, 2H), 7.42(d, J=8.6Hz, 2H), 7.02(d, J=7.5Hz, 1H), 6.68(d, J=7.4Hz, 1H) , 6.58(s, 1H), 3.86(t, J=5.4Hz, 2H), 3.77-3.68(m, 4H), 3.06-2.97(m, 4H), 2.31(s, 3H), 2.14(s, 3H ), 1.78-1.62 (m, 4H), 1.24 (s, 6H). ESI-MS: m / z 515.2 [M+Na] + .
Embodiment 3
[0107] 5-(2,5-Dimethylphenoxy)-1-(1-(4-((4-(trifluoromethyl)phenyl)sulfonyl)piperazinyl))-2,2-di Methyl-1-pentanone (Compound 4)
[0108] Compound 4 was obtained by referring to the method of Example 1: 1 H NMR (300MHz, CDCl 3 )δ7.83(d, J=8.1Hz, 2H), 7.71(d, J=8.2Hz, 2H), 7.02(d, J=7.4Hz, 1H), 6.68(d, J=7.3Hz, 1H) , 6.58(s, 1H), 3.86(t, J=5.2Hz, 2H), 3.81-3.70(m, 4H), 3.06(m, 4H), 2.31(s, 3H), 2.14(s, 3H), 1.79-1.61 (m, 4H), 1.24 (s, 6H). ESI-MS: m / z 549.2 [M+Na] + .
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More 
PatSnap Eureka turns technology decisions into work you can execute. Powered by our Innovation Knowledge Graph, it runs expert workflows across engineering, life sciences, materials and intellectual property. Get your review-ready output in minutes.
