Preparation and NMR spectroscopic studies of the glucuronides of Irbesartan

被引:12
作者
Byard, SJ
Herbert, JM
机构
[1] Sanofi Res, Dept Analyt Sci, Alnwick NE66 2JH, Northd, England
[2] Sanofi Res, Isotope Chem Labs, Alnwick NE66 2JH, Northd, England
[3] Sanofi Res, Dept Preclin Metab & Pharmacokinet, Alnwick NE66 2JH, Northd, England
关键词
angiotensin II antagonist; tetrazole glucuronide; nOe enhancement; C-13/H-1; correlation;
D O I
10.1016/S0040-4020(99)00255-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The preparation of N1- and N2-glucuronides of Irbesartan (SR47436) is described. The regiochemistry of the products was established from NMR spectroscopic studies, and the N2-glucuronide was identical to material obtained from natural sources. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5931 / 5936
页数:6
相关论文
共 14 条
[1]   A NEW SERIES OF IMIDAZOLONES - HIGHLY SPECIFIC AND POTENT NONPEPTIDE AT(1) ANGIOTENSIN-II RECEPTOR ANTAGONISTS [J].
BERNHART, CA ;
PERREAUT, PM ;
FERRARI, BP ;
MUNEAUX, YA ;
ASSENS, JLA ;
CLEMENT, J ;
HAUDRICOURT, F ;
MUNEAUX, CF ;
TAILLADES, JE ;
VIGNAL, MA ;
GOUGAT, J ;
GUIRAUDOU, PR ;
LACOUR, CA ;
ROCCON, A ;
CAZAUBON, CF ;
BRELIERE, JC ;
LEFUR, G ;
NISATO, D .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (22) :3371-3380
[2]   THE SYNTHESIS OF ARYL-D-GLUCOPYRANOSIDURONIC ACIDS [J].
BOLLENBACK, GN ;
LONG, JW ;
BENJAMIN, DG ;
LINDQUIST, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (12) :3310-3315
[3]   CHARACTERIZATION OF GLUCURONIC-ACID CONJUGATES OF A NOVEL ANGIOTENSIN RECEPTOR ANTAGONIST [J].
BOWERS, GD ;
EDDERSHAW, PJ ;
HUGHES, SY ;
MANCHEE, GR ;
OXFORD, J .
RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 1994, 8 (02) :217-221
[4]  
BUTLER RN, 1984, COMPREHENSIVE HETERO, V5, P791
[5]  
COLLETTI AE, 1994, DRUG METAB DISPOS, V22, P183
[6]   C-13 MAGNETIC-RESONANCE STUDIES OF AZOLES - TAUTOMERISM, SHIFT-REAGENT EFFECTS, AND SOLVENT EFFECTS [J].
ELGUERO, J ;
MARZIN, C ;
ROBERTS, JD .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (03) :357-363
[7]   Metabolites of the angiotensin II antagonist tasosartan: The importance of a second acidic group [J].
Ellingboe, JW ;
Collini, MD ;
Quagliato, D ;
Chen, J ;
Antane, M ;
Schmid, J ;
Hartupee, D ;
White, V ;
Park, CH ;
Tanikella, T ;
Bagli, JF .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (22) :4251-4260
[8]   CONTRASTERIC CARBOXIMIDE HYDROLYSIS WITH LITHIUM HYDROPEROXIDE [J].
EVANS, DA ;
BRITTON, TC ;
ELLMAN, JA .
TETRAHEDRON LETTERS, 1987, 28 (49) :6141-6144
[9]   Selective reactivity of sp3 and sp2 carbanions of 1-substituted 1,2,4-triazoles.: A comparative approach [J].
Katritzky, AR ;
Darabantu, M ;
Aslan, DC ;
Oniciu, DC .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (13) :4323-4331
[10]  
KOLBOBSKII GI, 1994, RUSS CHEM REV, V63, P797