NM 283, an efficient prodrug of the potent anti-HCV agent 2′-C-methylcytidine

被引:54
作者
Pierra, C
Benzaria, S
Amador, A
Moussa, A
Mathieu, S
Storer, R
Gosselin, G
机构
[1] Univ Montpellier 2, CNRS, Lab Cooperat Indenix, F-34095 Montpellier, France
[2] Lab Chim Med Indenix, Montpellier, France
[3] Idenix Pharmaceut Inc, Cambridge, MA USA
关键词
hepatitis C virus; 2 '-C-methyl branched nucleosides; prodrugs;
D O I
10.1081/NCN-200060112
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
In order to improve the oral bioavailability of 2'-C-methylcytidine, a potent anti-HCV agent, the corresponding 3'-O-L-valinyl ester derivative (NM 283) has been synthesized. Based on its ease Of synthesis and its physicochemical properties, NM 283 has emerged as a promising antiviral drug for treatment of chronic HCV infection.
引用
收藏
页码:767 / 770
页数:4
相关论文
共 10 条
[1]   ESTERIFICATION OF N-PROTECTED ALPHA-AMINO-ACIDS WITH ALCOHOL/CARBODIIMIDE/4-(DIMETHYLAMINO)-PYRIDINE - RACEMIZATION OF ASPARTIC AND GLUTAMIC-ACID DERIVATIVES [J].
DHAON, MK ;
OLSEN, RK ;
RAMASAMY, K .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (10) :1962-1965
[2]  
GODOFSKY E, 2004, 39 ANN M EUR ASS STU, P96
[3]   A short, flexible route toward 2'-C-branched ribonucleosides [J].
HarryOkuru, RE ;
Smith, JM ;
Wolfe, MS .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1754-1759
[4]   N-4-(DIALKYLAMINO)METHYLENE DERIVATIVES OF 5'-DEOXYCYTIDINE AND ARABINOCYTIDINE - PHYSICOCHEMICAL STUDIES FOR POTENTIAL PRODRUG APPLICATIONS [J].
KERR, SG ;
KALMAN, TI .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1994, 83 (04) :582-586
[5]   Conversion of uridine into 2′-O-(2-methoxyethyl)uridine and 2′-O-(2-methoxyethyl)cytidine [J].
Legorburu, U ;
Reese, CB ;
Song, QL .
TETRAHEDRON, 1999, 55 (17) :5635-5640
[6]   TERT-BUTYLDIMETHYLSILYL GROUP AS A PROTECTING GROUP IN DEOXYNUCLEOSIDES [J].
OGILVIE, KK .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1973, 51 (22) :3799-3807
[7]  
Sommadossi J., 2001, PREPARATION ANTIVIRA
[8]  
Sommadossi J.-P., 2001, METHODS COMPOSITIONS
[9]  
STANDRING DN, 2003, NM 283 HAS POTENT AN, P28
[10]   REMOVAL OF SILYL PROTECTING GROUPS FROM HYDROXYL FUNCTIONS WITH AMMONIUM FLUORIDE IN METHANOL [J].
ZHANG, WJ ;
ROBINS, MJ .
TETRAHEDRON LETTERS, 1992, 33 (09) :1177-1180