Macrocyclic quinoxaline compounds as HCV NS3 protease inhibitors
View Patent ↗The present invention relates to macrocyclic a compound of formula (I) and its use as inhibitors of the hepatitis C virus (HCV) NS3 protease, and in treating or preventing HCV infections.
1. A method of preparing a compound of formula (I):
said method comprising:
reacting (1aR,5S,8S,10R,22aR)-5-tert-butyl-14-methoxy-3,6-dioxo-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoxaline-8-carboxylic acid
with (1R,2S)-1-Amino-N-(cyclopropylsulfonyl)-2-vinylcyclopropanecarboxamide hydrochloride
2. The method of claim 1 , wherein the reacting is conducted in the presence of at least one reagent selected from the group consisting of diisopropylethylamine (DIEA), dimethylamino pyridine (DMAP) and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU).
3. The method of claim 1 , wherein the reacting is conducted in the presence of diisopropylethylamine (DIEA), dimethylamino pyridine (DMAP) and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU).
4. A method of preparing a pharmaceutically acceptable salt of a compound of formula (I):
said method comprising:
reacting a compound of formula (I) with a metal alkoxide to form a salt or the compound of formula (I).
5. The method of claim 4 , wherein the metal alkoxide is a potassium alkoxide.
6. The method of claim 5 , wherein the potassium alkoxide is a potassium tert-butoxide.
7. A compound prepared by the method of claim 1 .
8. A compound prepared by the method of claim 4 .