SYNTHESIS OF NEVIRAPINE AND ITS MAJOR METABOLITE

被引:19
作者
GROZINGER, KG
FUCHS, V
HARGRAVE, KD
MAULDIN, S
VITOUS, J
CAMPBELL, S
ADAMS, J
机构
[1] Boehringer Ingelheim Pharmaceuticals, Inc, Process Chemistry Research, Ridgebury, Connecticut, 06877-0368
[2] Eli Lilly, Indianapolis, Indiana
[3] MyoGenics Inc, Cambridge, Massachusetts, 02139
关键词
D O I
10.1002/jhet.5570320144
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Several synthetic methods were developed during the process optimization for the large scale synthesis of nevirapine (1), a non-nucleoside inhibitor of HIV-1 Reverse Transcriptase. The synthesis of its putative major metabolite 11-cyclopropyl-5,11-dihydro-4-hydroxymethyl-6H-[3,2-b:2',3'-e][1,4]diazepin-6-one (2) and the oxidation of 2 to the corresponding aldehyde 3, are described.
引用
收藏
页码:259 / 263
页数:5
相关论文
共 25 条
[1]   DECHLORINATION OF SOME CHLORONITROPICOLINES [J].
BAUMGARTEN, HE ;
SU, HCF ;
KRIEGER, AL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (02) :596-599
[2]   NAPHTHYRIDINES .2. SYNTHESIS OF 1,7-NAPHTHYRIDINES BY BORSCHE SYNTHESIS [J].
BAUMGARTEN, HE ;
COOK, KC .
JOURNAL OF ORGANIC CHEMISTRY, 1957, 22 (02) :138-140
[3]   ANTIMALARIAL 2-ALKOXY-6-CHLORO-9-DIALKYLAMINOALKYLAMINO-1-10-DIAZA-ANTHRACENES [J].
BESLY, DM ;
GOLDBERG, AA .
JOURNAL OF THE CHEMICAL SOCIETY, 1954, (JUL) :2448-2455
[4]   SYNTHESIS OF ISOQUINOLINE ALKALOIDS .2. THE SYNTHESIS AND REACTIONS OF 4-METHYL-3-PYRIDINECARBOXALDEHYDE AND OTHER 4-METHYL-3-SUBSTITUTED PYRIDINES [J].
BOBBITT, JM ;
SCOLA, DA .
JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (04) :560-564
[6]  
BURTON AG, 1971, TETRAHEDRON LETT, P2211
[7]   PYRAZOLOPYRIDINES .5. PREPARATION AND REACTIONS OF PYRAZOLO-[3,4-C]PYRIDINES [J].
CHAPMAN, D ;
HURST, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (11) :2398-2402
[8]   PHARMACOKINETICS OF NEVIRAPINE - INITIAL SINGLE-RISING-DOSE STUDY IN HUMANS [J].
CHEESEMAN, SH ;
HATTOX, SE ;
MCLAUGHLIN, MM ;
KOUP, RA ;
ANDREWS, C ;
BOVA, CA ;
PAV, JW ;
ROY, TP ;
SULLIVAN, JL ;
KEIRNS, JJ .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1993, 37 (02) :178-182
[9]   TRAPPING OF PICOLYL CATIONS IN REACTIONS OF 2-PICOLINE AND 4-PICOLINE N-OXIDE WITH ACETIC-ANHYDRIDE [J].
COHEN, T ;
DEETS, GL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (03) :932-&
[10]   NOVEL NONNUCLEOSIDE INHIBITORS OF HIV-1 REVERSE-TRANSCRIPTASE .1. TRICYCLIC PYRIDOBENZODIAZEPINONES AND DIPYRIDODIAZEPINONES [J].
HARGRAVE, KD ;
PROUDFOOT, JR ;
GROZINGER, KG ;
CULLEN, E ;
KAPADIA, SR ;
PATEL, UR ;
FUCHS, VU ;
MAULDIN, SC ;
VITOUS, J ;
BEHNKE, ML ;
KLUNDER, JM ;
PAL, K ;
SKILES, JW ;
MCNEIL, DW ;
ROSE, JM ;
CHOW, GC ;
SKOOG, MT ;
WU, JC ;
SCHMIDT, G ;
ENGEL, WW ;
EBERLEIN, WG ;
SABOE, TD ;
CAMPBELL, SJ ;
ROSENTHAL, AS ;
ADAMS, J .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (07) :2231-2241