CAS: 196618-13-0; (3R,4R,5S)-Ethyl 4-Acetamido-5-Amino-3-(Pentan-3-Yloxy)Cyclohex-1-Enecarboxylate

上下游产品

oseltamivir ethyl (3R,4R,5S)-4-N-acetylamino-5-N-allylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-(1-ethylpropoxy)cyclohex-3-en-1-yl]carbamate ethanol(3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate oseltamivir acid (3R,4R,5S)-5-(acetylamino)-4-amino-3-(pentan-3-yloxy) cyclohex-1-ene-1-carboxylic acid oseltamivir phosphate

磷酸奥司他韦置于碳酸氢钠体系中,用 水 用作溶剂,化学反应 0.08H,以98%的收率获得奥司他韦
参考文献:替米磷与h1N1(2009)大流行性流感的神经氨酸酶结合的动力学,热力学和结构分析
标题:替米磷与h1N1(2009)大流行性流感的神经氨酸酶结合的动力学,热力学和结构分析
摘要:流感病毒会引起严重的呼吸道感染,每年导致全球多达100万人死亡.迄今为止,已批准了两种靶向病毒神经氨酸酶的抑制剂(奥司他韦,扎那米韦).然而,抗病毒药物耐药性的迅速发展和人类之间抗病毒的有效传播对公共卫生构成了严重威胁. 批准的流行性感冒神经氨酸酶抑制剂具有(oxa)环己烯骨架,可模拟唾液酸酶切过程中的氧鎓过渡态.它们的活性形式包含与酶活性位点中的三个精氨酸残基相互作用的羧酸盐.最近,膦酸酯基团成功地用作了奥司他韦中羧酸酯的等排物,并且将所得的化合物他米磷酯鉴定为高活性神经氨酸酶抑制剂.然而,尚未报道该有希望的抑制剂与神经氨酸酶的复合物的结构. 在这里,我们分析了一套oseltamivir和tamiphosphor衍生物与来自a / California / 07/2009(h1N1)流感病毒的神经氨酸酶的相互作用.我们通过蛋白质微量量热法热力学表征了奥司他韦羧酸盐或他米磷与神经氨酸酶催化
Doi:10.1016/j.Ejmech.2016.05.016

专利信息

专利号:US-9353057-B2
优先权日:2003-12-30
标 题:Synthesis of acyloxyalkyl carbamate prodrugs and intermediates thereof
发明人：GALLOP MARK A; DAI XUEDONG; SCHEUERMAN RANDALL A; RAILLARD STEPHEN P; MANTHATI SURESH K; YAO FENMEI; PHAN THU; LUDWIKOW MARIA; PENG GE; BHAT SEEMA
权利人:XENOPORT INC
摘要:Methods for synthesis of 1-(acyloxy)-alkyl carbamates, particularly, the synthesis of 1-(acyloxy)-alkyl carbamate prodrugs of primary or secondary amine-containing drugs are described. Also described are methods for synthesis of 1-(acyloxy)-alkyl N-hydroxysuccinimidyl carbonates which are useful intermediates in the synthesis of 1-(acyloxy)-alkyl carbamates are also described.

专利号:US-2024024497-A1
优先权日:2020-08-06
标 题:Methods for the synthesis of protein-drug conjugates
发明人：BORCHARDT ALLEN; HUGHES ROBERT MICHAEL
权利人:CIDARA THERAPEUTICS INC
摘要:The present invention relates to methods for the synthesis of conjugates useful for the treatment of viral infections, e.g., conjugates containing inhibitors of viral neuraminidase (e.g., zanamivir or an analog thereof) linked to an Fc domain monomer.

专利号:US-7888337-B2
优先权日:2007-08-31
标 题 :Synthesis of oseltamivir containing phosphonate congeners with anti-influenza activity
发明人：WONG CHI-HUEY; FANG JIM-MIN; SHIE JIUN-JIE; CHENG YIH-SHYUN EDMOND; JAN JIA-TSRONG
权利人:ACADEMIA SINICA
摘要:Novel phosphonate compounds are described. The compounds have activity as neuraminidase inhibitors against wild-type and H274Y mutant of H1N1 and H5N1 viruses. The present disclosure also provides an enantioselective synthetic route to known neuraminidase inhibitors oseltamivir and the anti-flu drug Tamiflu®, as well as novel phosphonate compounds, via D-xylose. Another efficient and flexible synthesis of Tamiflu and the highly potent neuraminidase inhibitor Tamiphosphor was also achieved in 11 steps and >20% overall yields from the readily available fermentation product (1S-cis)-3-bromo-3,5 -cyclohexadiene-1,2-diol. Most of the reaction intermediates were obtained as crystals without tedious purification procedures. The key transformations include an initial regio- and stereoselective bromoamidation of a bromoarene cis-dihydrodiol, as well as the final palladium-catalyzed carbonylation and phosphonylation.

专利号:WO-2025101716-A1
优先权日:2023-11-07
标题:Processes for synthesis of trifunctionalized sulfur(vi) compounds
发明人：LOPCHUK JUSTIN; SHULTZ ZACHARY; ATHAWALE PARESH
权利人:H LEE MOFFITT CANCER CT & RES
摘要:This disclosure describes processes for the asymmetric synthesis of trifunctionalized sulfur(VI) containing organic compounds of Formula I and Formula VI, as well as compounds of Formula I and Formula VI prepared by the processes described.

专利号:US-11311505-B2
优先权日:2017-02-24
标 题:Synergistic compositions to stimulate the synthesis of human lung and sinus surfactants to decrease coughing, increase FEV-1/FVC ratios, decrease lung fibrosis, by increasing apoptosis of myofibroblasts
发明人：MARTIN ALAIN
权利人:MARTIN ALAIN; CELLULAR SCIENCES INC
摘要:Methods for the treatment of patients with both Chronic Obstructive Pulmonary Disease (COPD) and pulmonary fibrosis, and of patients with idiopathic pulmonary fibrosis without COPD, by stimulating the synthesis of human and animal patient lung and sinus surfactants to increase lung functions, inhibiting fibrosis and reducing coughing and nasal erythema, include the following steps: A) analyzing and diagnosing a patient with a lung ailment selected from the group consisting of i) both COPD and pulmonary fibrosis; and ii) idiopathic pulmonary fibrosis without COPD; and, B) treating the patient to raise the patient's lung functions including FEV1/FVC ratio by contacting mammalian cells with a [therapeutically effective amount of a treatment] composition that includes: a) a pyruvate salt; b) a phosphate; c) a salt of calcium; and d) a salt of magnesium, in an aqueous carrier, containing no more than 2.2 grams of said pyruvate salt per liter.

专利号:WO-2011097717-A1
优先权日:2010-02-15
标 题 :Synthesis of bicyclic compounds and method for their use as therapeutic agents
发明人：WULFF JEREMY EARLE; BRANT MICHAEL GLENN; BROMBA CALEB MATTHEW; BOULANGER MARTIN JOHN
权利人:UNIV VICTORIA INNOVAT DEV; WULFF JEREMY EARLE; BRANT MICHAEL GLENN; BROMBA CALEB MATTHEW; BOULANGER MARTIN JOHN
摘要:Disclosed embodiments concern the synthesis and use of therapeutic compounds that for treating emerging flu strains and minimizing resistance to such strains. Methods for making the disclosed compounds concern using a base-mediated addition/cyclization sequence followed by functional group manipulation to develop functionalized compounds that can target neuraminidase, which makes them ideal candidates for treating influenza. Pharmaceutical compositions comprising the therapeutic compounds and biologically-acceptable materials are also described. Methods of inhibiting neuraminidase in subjects that are suspected of containing neuraminidase are also described. The use of metabolites of the disclosed compounds can also be used in diagnostic assays for therapeutic dosing of the disclosed compounds.