89288-25-5Relevant academic research and scientific papers
Synthesis method of nitrendipine metabolite
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Paragraph 0049; 0051, (2018/08/03)
The invention discloses a synthesis method of nitrendipine metabolite. The method takes 4-(benzyloxy)-3-ethyl oxo-butyrate and 3-hydroxypropionitrile as starting raw materials to synthesize the nitrendipine metabolite through 6-step reaction. A lot of experiments are carried out to screen optimal preparation steps and reaction conditions; a whole technology is reasonably designed and strong in operability; the chemical purity of the nitrendipine metabolite prepared by the synthesis method can reach 99 percent or more and the yield is high. The nitrendipine metabolite prepared by the synthesismethod provides a standard product for metabolic mechanism researches of a nitrendipine medicine and can be used for exploring a metabolic process of the medicine in organisms; the nitrendipine metabolite has a relatively good potential hypertension-resisting effect and has extremely application and research value in clinical pharmacokinetics researches.
3-(Nitrobenzylidene)-2,4(3H,5H)-furandiones in the Hantzsch pyridine synthesis, part 1.: A new approach to furo[3,4-b]pyridines
Goerlitzer,Bartke
, p. 672 - 678 (2007/10/03)
The nitrobenzylidenefurandiones 7 react with acetoacetic ester (8) and ammonium acetate or 3-aminocrotonic esters (9a, b) and 2-aminopent-2-en-4-on (9c), respectively heating in acetic acid to yield the tetrahydrofuro[3,4-b] pyridines 10. The dehydrogenation of 10 using nitric acid or activated manganese dioxide leads to the dihydrofuro[3,4-b]pyridines 12. When the reaction is carried out with the tetronic acid derivatives 7 and the enaminocarbonyl compounds 9 at 30°C in tert-butanol the hexahydro-7a-hydroxyfuro[3,4-b]pyridines 11 are obtained. Treating the N,O-acetales 11 with acetic anhydride in pyridine affords the annulated lactones 10.
Biotransformation of nitrendipine in rat, dog, and mouse
Scherling,Karl,Ahr,Kern,Siefert
, p. 1009 - 1021 (2007/10/02)
14C-Labelled Nitrendipine (Bay e 5009; Baypress, Bayotensin; CAS 39562-70-4) was administered by the oral and intraduodenal route to rats, dogs, and mice (oral dosing only) to elucidate the biotransformation pathways in these three species. The drug was extensively metabolized: 20 biotransformation products were identified by comparison with synthetic reference compounds using two-dimensional TLC, HPLC, GC/radio-GC, combined GC/MS (EI-, CI-mode), FAB-MS, and 1H-NMR-spectroscopy. The metabolites identified accounted for approx. 72 to 73% of the dose administered in rats and dogs (bile and urine) and 48 to 56% in male and female mice (urine only). Based on the structures identified the following biotransformation reactions occurred: Dehydrogenation of the 1,4-dihydropyridine (primary metabolic step), oxidative ester cleavage as further basic biotransformation reaction (also at the dihydropyridine state), hydroxylation of the methyl groups in 2- or 6-position as separated and important metabolic reaction (at the dihydropyridine as well as pyridine state), reduction of the aromatic nitro group (important only in mice) and subsequent acetylation (dog only), and glucuronidation as phase II reaction forming ether and ester type glucuronides.
Nitrendipine: Identification and synthesis of main metabolites
Meyer,Scherling,Karl
, p. 1528 - 1534 (2007/10/02)
(±)-Ethylmethyl-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridined icarboxylate (nitrendipine, Baye e 5009) 1, a calcium antagonistic 1,4-dihydropyridine derivative, is currently under development as an antihypertensive. A pharmacokinetic study with
