Biomarkers for determining effective response of treatments of hepatocellular carcinoma (HCC) patients
A biomarker, patient technology, applied in the direction of medical preparations containing active ingredients, amide active ingredients, biomaterial analysis, etc.
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0321] Example 1 : N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)phenyl)-1-(2,3-dihydroxypropyl)cyclopropane-1-sulfonamide:
[0322] Step A: Butyl cyclopropanesulfonate :
[0323]
[0324] Cyclopropanesulfonyl chloride (5g, 35mmol, 1eq) was dissolved in excess BuOH (20ml), the reaction mixture was cooled at -10°C, and pyridine (5.8mL, 70mmol, 2eq) was slowly added dropwise. The mixture was slowly warmed to room temperature and stirred overnight. The solvent was removed under reduced pressure, and the resulting white solid was dissolved in CHCl 3 dissolved in. The organic phase was washed with water, brine, and dried (MgSO 4 ) and concentrated to give an oil (4.8 g, 24.9 mmol, 71%). 1 H NMR (300MHz, CDCl 3 ): δ4.25(t,2H),2.46(m,1H),1.74(m,2H),1.45(m,2H),1.25(dd,2H),1.09(dd,2H),.93(t ,3H).
[0325] Step B: Butyl 1-allylcyclopropane-1-sulfonate :
[0326]
[0327] To a solution of 1-butylcyclopropanesulfonate (4.8g, 24.9mmol) in THF was simultaneously added a ...
Embodiment 1A
[0340] Example 1A : (S)-N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)phenyl)-1-(2,3-dihydroxypropyl)cyclopropane-1- Sulfonamide:
[0341]
[0342] The pure S isomer was obtained by chiral HPLC separation of the racemic mixture (Example 13). 1 H NMR (300MHz, CDCl 3 +D 2 O): δ7.38(dd, J=1.8&10.5Hz, 1H), 7.36(ddd, J=2.4, 5.1&9.3Hz, 1H), 7.25(d, J=8.7Hz, 1H), 7.02(dd ,J=9.0&17.7Hz,1H),6.27(dt,J=3.0,8.7&17.4Hz,1H),3.92(m,1H),3.54(dd,J=3.9&11.1Hz,1H),3.39( dd, J=6.6&11.1Hz, 1H), 2.16(dd, J=9.6&15.9Hz, 1H), 1.59(d, J=14.1Hz, 1H), 1.41(m, 1H), 1.26(m, 1H ),0.83(m,2H); m / z=542[M-1] - .
Embodiment 1B
[0343] Example 1B : Example 1A: (R)-N-(3,4-difluoro-2-(2-fluoro-4-iodophenylamino)phenyl)-1-(2,3-dihydroxypropyl) ring Propane-1-sulfonamide:
[0344]
[0345]The pure R isomer was obtained by chiral HPLC separation of the racemic mixture (Example 13). 1 H NMR (300MHz, CDCl 3 +D 2 O): δ7.38(dd, J=1.8&10.5Hz, 1H), 7.36(ddd, J=2.4, 5.1&9.3Hz, 1H), 7.25(d, J=8.7Hz, 1H), 7.02(dd ,J=9.0&17.7Hz,1H),6.27(dt,J=3.0,8.7&17.4Hz,1H),3.92(m,1H),3.54(dd,J=3.9&11.1Hz,1H),3.39( dd, J=6.6&11.1Hz, 1H), 2.16(dd, J=9.6&15.9Hz, 1H), 1.59(d, J=14.1Hz, 1H), 1.41(m, 1H), 1.26(m, 1H ),0.83(m,2H); m / z=542[M-1] - .
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More 