CAS: 89365-50-4; 2-(Hydroxymethyl)-4-(1-Hydroxy-2-{[6-(4-Phenylbutoxy)Hexyl]Amino}Ethyl)Phenol
该化合物是一种长效的β-2-肾紧张受体激动剂(ABA),主要用于治疗哮喘和慢性阻塞性肺病(COPD),其主要优势在于其长期支气管结扎效应,由于其高脂性和持续的受体结合,这种效应长达12小时,持续持续持续.Salmeterol 经常与吸入的碳原子固醇相结合,以产生协同抗炎和支气管阻塞效应,改进症状控制并减少加速频率.它选择性的β-2强力将心脏侧效应与非选择性的抗生素动物相比降到最低.该药物通过吸入方式施用,确保有针对性地交付肺部,同时尽量减少系统接触.Salmeterol 的药理基因特征使它成为阻塞性空气疾病保持治疗的基石.
- ⚠️《2026年兴奋剂目录》
- 英文名称2-(Hydroxymethyl)-4-(1-Hydroxy-2-{[6-(4-Phenylbutoxy)Hexyl]Amino}Ethyl)Phenol
- 中文名称沙美特罗
- IUPAC名称4-Hydroxy-alpha1-[[[6-(4-phenylbutoxy)hexyl]amino]methyl]-1,3-benzenedimethanol
- 其它别名2-(Hydroxymethyl)-4-[1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino] ethyl]-phenol
- CAS编号89365-50-4
- MFCD编号:MFCD00867037
- EINECS号:618-267-2
- FDA UNII编号:2I4BC502BT
- 分子式:C25H37NO4
- 分子量:415.57
- 产品CID: 1915090
- 同类组份化合物CAS89365-50-4 (free base)94749-08-3 (xinafoate)
- 产品分类原料药 → 呼吸系统用药 → 平喘药
物理性质
- 熔点75.5-76.5°
- 沸点603.0±55.0 °C(预测)
- 闪点318.5 °C
- 密度1.112±0.06 g/cm3(预测)
- pKa:9.99±0.31(预测)
- PSA:81.95
- LogP:4.4983
- 蒸汽压1.9X10-15 mm Hg at 25 °C /Estimated/
- 溶解性Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
- 外观形态白色至类白色固体
- 储存条件2-8°C
- 产品应用沙美特罗(89365-50-4)的用途:该药是长效选择性β2-肾上腺受体激动剂,产生明显的气管扩张作用.用于长期常规治疗哮喘的可逆性呼吸道阻塞和慢性支气管炎.
- 性质描述沙美特罗(89365-50-4)的性状:1.熔点75.5～76.5°C.2.昔萘酸沙美特罗(Salmeterol Xinafoate):C25H37NO4・C11H8O3.为沙美特罗(89365-50-4)的1-羟基-2-萘甲酸盐.熔点138°C.易溶于甲醇,微溶于乙醇,氯仿或异丙醇,难溶于水.
MSDS等安全信息
欧盟法规
C&L通报REACH预注册上下游产品
4-hydroxy-1-[[[6-(4-phenylbutoxy)hexyl](phenylmethyl)amino]methyl]-1,3-benzenedimethanol H-benzo[1,3]dioxin-6-yl)-2-[6-(4-phenyl-butoxy)-hexylamino]-ethanol1-(4H-benzo[1,3]dioxin-6-yl)-2-[6-(4-phenyl-butoxy)-hexylamino]-ethanol H-benzo[1,3]dioxine6-oxiranyl-4H-benzo[1,3]dioxine 6-ω-bromoacetyl-1,3-benzodioxanesalmeterol xinafoate (S)-Salmeterol (R)-(-)-salmeterol合成工艺路线路线简述
- 合成目标产物 Salmeterol 主要起始原料 N, O-Dibenzyl Salmeterol
- 89365-50-4 + 86-48-6 = 89365-50-4 + 86-48-6
反应条件:1.1 Solvents: Methyl Ethyl Ketone; Rt
标题:Process For The Preparation Of Salmeterol Xinafoate From 2-(Bromoethyl)Benzene
参考文献:China]
89365-50-4 + 86-48-6 = 89365-50-4 + 86-48-6
反应条件:1.1 Solvents: Acetone; 40 Min,30 °C
标题:Preparation Method Of Salmeterol Xinafoate
参考文献:China]
934842-69-0 + 86-48-6 = 89365-50-4 + 86-48-6
反应条件:1.1 Solvents: Ethanol; Rt
标题:A New Route For Synthesis Of Salmeterol Xinafoate
作者:Wu,Xiaochun
参考文献:Xinan Shifan Daxue Xuebao 日期:2009 卷标:34(4) 页码:85-88]
262857-01-2 + 86-48-6 = 89365-50-4 + 86-48-6
反应条件:1.1 Reagents: Acetic Acid Solvents: Water; 3 H,70 °C1.2 Solvents: Ethyl Acetate; 16 H,Rt
标题:Preparation Of Deuterium Substituted Ethanolamines As Adrenergic Modulators For Disease Treatment
参考文献:United States]
= 89365-50-4 + 86-48-6 [标题:Reaction Conditions
标题:Utility Of Von Pechman Synthesis Of Coumarin Reaction For Development Of Spectrofluorimetric Method For Quantitation Of Salmeterol Xinafoate In Pharmaceutical Preparations And Human Plasma
作者:Awad,Mohamed; Hammad,Mohamed A.; Abdel-Megied,Ahmed M.; Omar,Mahmoud A.
参考文献:Luminescence 日期:2018 卷标:33(5) 页码:913-918]
= 89365-50-4 + 86-48-6 [标题:Reaction Conditions
标题:An Improved Process For The Preparation Of Salmeterol Xinafoate
参考文献:India]
2691147-83-6 = 89365-50-4
反应条件:1.1 Reagents: Lithium Aluminum Hydride Solvents: Diethyl Ether; Rt; 1 H,Rt1.2 Reagents: Water
标题:Structural Isomers Of Saligenin-Based β2-Agonists: Synthesis And Insight Into The Reaction Mechanism
作者:Knezevic,Anamarija; Novak,Jurica; Bosak,Anita; Vinkovic,Marijana
参考文献:Organic & Biomolecular Chemistry 日期:2020 卷标:18(47) 页码:9675-9688]
934842-69-0 = 89365-50-4
反应条件:1.1 Reagents: Formic Acid Catalysts: Palladium Solvents: Methanol; Overnight,35 °C
标题:A New Route For Synthesis Of Salmeterol Xinafoate
作者:Wu,Xiaochun
参考文献:Xinan Shifan Daxue Xuebao 日期:2009 卷标:34(4) 页码:85-88]
727641-92-1 + 94749-73-2 = 89365-50-4
反应条件:1.1 Reagents: Triethylamine Catalysts: Potassium Iodide Solvents: Dimethylformamide; 12 H,80 °C
标题:Study On The Process For Synthesis Of Salmeterol
作者:Shen,Li-Qun
参考文献:Guangzhou Huagong 日期:2008 卷标:36(4) 页码:46-47]
97664-54-5 + 915132-89-7 = 89365-50-4
反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol; Overnight,2.06 Mpa,Rt1.2 Reagents: Acetic Acid Solvents: Methanol; 48 H,40 °C1.3 Reagents: Sodium Bicarbonate Solvents: Water
标题:New Synthetic Route To Salmeterol
作者:Zhou,Di; Liu,Juntao; Lu,Yixiang; Jia,Xian; Li,Xingshu
参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2009 卷标:19(2) 页码:123-125]
97664-58-9 + 1239368-65-0 = 89365-50-4
反应条件:1.1 Solvents: Ethanol; 12 H,Reflux; Reflux -> Rt1.2 Reagents: Sodium Borohydride; 24 H,Rt
标题:The Synthesis Of Salmeterol
作者:Ying,Min; Zhang,Huaxing
参考文献:Guangdong Huagong 日期:2009 卷标:36(12)]
89365-50-4 + 86-48-6 = 89365-50-4 + 86-48-6
反应条件:1.1 Solvents: Acetone; 3 - 4 H,25 - 35 °C
标题:Preparation Of Salmeterol And Salts Thereof
参考文献:India]
89365-50-4 + 86-48-6 = 89365-50-4 + 86-48-6
反应条件:1.1 Solvents: Acetone; 30 Min,45 °C; 45 °C -> 25 °C; 1 H,25 °C1.2 Solvents: Tert-Butyl Methyl Ether; 25 °C -> 10 °C; 2 H,10 °C
标题:Process For Preparation Of Salmeterol
参考文献:World Intellectual Property Organization]
89365-50-4 + 86-48-6 = 89365-50-4 + 86-48-6
反应条件:1.1 Solvents: Methanol; 1 H,30 °C; 30 °C -> 22 °C; 2 H,18 - 22 °C
标题:Improved Process For The Preparation Of Salmeterol Xinafoate
参考文献:India]
89365-50-4 + 86-48-6 = 89365-50-4 + 86-48-6
反应条件:1.1 Solvents: Methanol; 25 - 30 °C; 3 H,0 °C
标题:A Method For Preparing Salmeterol Hydroxynaphthoate
参考文献:China]
89365-50-4 + 86-48-6 = 89365-50-4 + 86-48-6
反应条件:1.1 Solvents: Methanol,Ethyl Acetate
标题:Preparation Of Salmeterol Xinafolate
作者:Anonymous
参考文献:Research Disclosure 日期:2006 卷标:506]
89365-50-4 + 86-48-6 = 89365-50-4 + 86-48-6
反应条件:1.1 Solvents: Isopropanol; Rt -> 70 °C; 8 H,70 °C
标题:Synthesis Route Of Salmeterol Xinafoate
作者:Jiang,Zhi-Gan; Hua,Zheng-Mao; Mai,Lu-Gen; Yang,Li-Ge
参考文献:Huadong Shifan Daxue Xuebao 日期:2003 卷标:(3) 页码:102-104]
= 89365-50-4 + 86-48-6 [标题:Reaction Conditions
标题:Preparation Of Salmeterol And Its Application
参考文献:China]
= 89365-50-4 + 86-48-6 [标题:Reaction Conditions
标题:Improved Process For The Preparation A Long-Acting β2-Adrenergic Agonist (Laba) Salmeterol And Identification,Characterization And Control Of Its Potential Process Impurity
作者:Reddy,Sahadeva; Rajan,S. T.; Parusuramudu; Reddy,Raghupathi; Chakravarthy,I. E.
参考文献:Pharma Chemica 日期:2016 卷标:8(8) 页码:28-35]
= 89365-50-4 + 86-48-6 [标题:Reaction Conditions
标题:Process For The Preparation Of Crystalline Salmeterol And Its Xinafoate Salt
参考文献:World Intellectual Property Organization]
= 89365-50-4 + 86-48-6 [标题:Reaction Conditions
标题:Process For Preparation Of Salmeterol
参考文献:India]
= 89365-50-4 + 86-48-6 [标题:Reaction Conditions
标题:Process For Preparation Of Salmeterol Xinafoate
参考文献:World Intellectual Property Organization]
= 89365-50-4 + 86-48-6 [标题:Reaction Conditions
标题:Medicaments Containing Betamimetic Drugs And A Novel Anticholinesterase Drug For Treating Respiratory Tract Diseases
参考文献:World Intellectual Property Organization]
= 89365-50-4 + 86-48-6 [标题:Reaction Conditions
标题:Phenethanolamine Derivatives Useful In The Treatment Of Respiratory Problems
参考文献:Federal Republic Of Germany]
934842-69-0 = 89365-50-4
反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol; 36 H,58 Psi,45 °C
标题:An Efficient And Practical Synthesis Of Salmeterol
作者:Lu,Yongping; Xu,Xinliang; Zhang,Xingxian
参考文献:Organic Preparations And Procedures International 日期:2015 卷标:47(2) 页码:168-172]
27475-14-5 + 97664-55-6 = 89365-50-4
反应条件:1.1 Reagents: Sodium Carbonate Solvents: Dichloromethane,Water; 10 Min,Ph 8 - 9,25 - 35 °C1.2 Reagents: Diisopropylethylamine; 25 - 35 °C; 4 H,25 - 35 °C1.3 Reagents: Vitride Solvents: Toluene; 35 °C -> 5 °C; 1 H,0 - 5 °C1.4 Reagents: Monopotassium Monosodium Tartrate Tetrahydrate Solvents: Water; 0 - 5 °C; 1 H,25 - 35 °C1.5 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol; 2 H,25 - 35 °C
标题:Improved Process For The Preparation A Long-Acting β2-Adrenergic Agonist (Laba) Salmeterol And Identification,Characterization And Control Of Its Potential Process Impurity
作者:Reddy,Sahadeva; Rajan,S. T.; Parusuramudu; Reddy,Raghupathi; Chakravarthy,I. E.
参考文献:Pharma Chemica 日期:2016 卷标:8(8) 页码:28-35]
163923-19-1 = 89365-50-4
反应条件:1.1 Reagents: Sodium Borohydride Solvents: Methanol1.2 Reagents: Hydrochloric Acid Solvents: Water1.3 Reagents: Sodium Carbonate Solvents: Water1.4 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol
标题:A New Synthetic Approach To Salmeterol
作者:Rong,Yajing; Ruoho,Amold E.
参考文献:Synthetic Communications 日期:1999 卷标:29(12) 页码:2155-2162
Methyl 5-{2-[6-(4-Phenyl-Butoxy)-Hexylamino]-1-Hydroxy-Ethyl}Salicylate置于lithium Aluminium Tetrahydride体系中,用 乙醚 作为反应溶剂,化学反应 1.0H,以87%的收率获得产物沙美特罗
参考文献:基于水杨苷的β2-激动剂的结构异构体:合成和反应机制的洞察
标题:基于水杨苷的β2-激动剂的结构异构体:合成和反应机制的洞察
摘要:沙美特罗和沙丁胺醇是众所周知的β2-腺受体激动剂,广泛用于治疗炎症性呼吸道疾病,例如支气管哮喘和慢性阻塞性肺病.在这里,我们报道了沙美特罗和沙丁胺醇结构异构体的制备,它们可以从与相应的β2-激动剂相同的起始材料中获得,具体取决于所采用的合成方法.使用一维和各种二维核磁共振测量,我们确定所制备的异构体的结构含有β-芳基-β-氨基乙醇部分,与沙美特罗和沙丁胺醇中发现的α-芳基-β-氨基乙醇部分相反.我们通过实验和计算方法研究了 β-卤代醇和胺的反应,该反应负责形成 β-芳基-β-氨基醇.具有水杨酸甲酯部分的β-卤代醇的结构决定了反应的进程.溶剂在反应方向上起着相关但模糊的作用,而碱的强度以更明显的方式影响反应产率和异构体比例.使用计算方法,我们已经表明,最有可能导致意外异构体形成的反应中间体是相应的对醌甲基化物,其可以由于水杨酸甲酯部分中存在的苯酚而形成.成功制备沙丁胺醇和沙美特罗异构体后,我
DOI:10.1039/d0Ob02095H
海关参考信息
- 2902600000-乙苯
2905121000-正丙醇
2905130000-正丁醇
2906210000-苄醇 - 💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
- 详情请参考：📖 海关编码查询和海关进出口税则
专利信息
专利号:US-2006167025-A1
优先权日:2004-12-22
标 题:Tricyclic amino alcohols, processes for synthesis of same and use of same as anti-inflammatory drugs
发明人：BERGER MARKUS; SCHMEES NORBERT; SCHAECKE HEIKE; BAURLE STEFAN; REHWINKEL HARTMUT; MENGEL ANNE; KROLIKIEWICZ KONRAD; GROSSBACH DANJA; VOIGTLAENDER DAVID
权利人:BERGER MARKUS; SCHMEES NORBERT; SCHAECKE HEIKE; BAURLE STEFAN; REHWINKEL HARTMUT; MENGEL ANNE; KROLIKIEWICZ KONRAD; GROSSBACH DANJA; VOIGTLAENDER DAVID
摘要:The invention relates to tricyclic amino alcohols of general formula (I) n nmethod for synthesis of same and use of same as anti-inflammatory agents.
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:US-5442118-A
优先权日:1994-04-22
标题 :Asymmetric synthesis of (R)- and (S)-arylethanolamines from iminoketones
发明人：GAO YUN; HONG YAPING; ZEPP CHARLES M
权利人:SEPRACOR INC
摘要:A method for the enantioselective reduction of an alpha -iminoketone to an alpha -aminoalcohol is disclosed. The method utilizes a borane reducing agent as the reducing agent and a chiral 1,3,2-oxazaborole as the catalyst. The method is applied to the synthesis of R-albuterol from methyl 5-acetylsalicylate in high yield and high optical purity.
专利号:US-2025206743-A1
优先权日:2022-03-25
标 题:Tyk2 inhibitor synthesis and intermediates thereof
发明人：MASSE CRAIG E; PHADKE AVINASH S; LAWSON JON P; LEVY STUART; YANG XIAOWEI; WU GUISHENG; FAN SHUFENG
权利人:TAKEDA PHARMACEUTICALS CO
摘要:Described herein are methods of synthesis of a tyrosine-protein kinase 2 (TYK2) inhibitor and to intermediate compounds of the synthesis and methods of making the intermediates. Also provided are pharmaceutically acceptable compositions including compounds prepared by the synthetic method and methods of treating disorders using the same.
专利号:US-10813893-B2
优先权日:2017-02-24
标 题:Compositions and methods for the treatment and prevention of chronic hypoxemia and dyspnea
发明人：MARTIN ALAIN
权利人:MARTIN ALAIN; CELLULAR SCIENCES INC
摘要:The present invention has shown that not all salts of pyruvic acid enhance lung functions or enhance the synthesis of lung surfactants and that certain salts of pyruvic acid with the correct concentrations of calcium, phosphate and magnesium, are synergistic in their ability to enhance the synthesis of lung surfactants that will enhance lung alveoli functions, while decreasing coughing and lung tightness, and increasing oxygen saturation values to prevent hypoxemia. This patent demonstrates that the sodium pyruvate formula with calcium, phosphate and magnesium was superior over standard sodium pyruvate formula in saline alone in the removal of mucus, reduction of lung or sinus infections, and in reducing drug side effects and congestion. The use of this formula clearly demonstrated that it can be used to produce better efficacy in patients with hypoxemia, with lung and sinus diseases including, asthma, COPD, cystic fibrosis, interstitial lung disease, allergic rhinitis, sinusitis, Alzheimer's, disease, Parkinson's disease, brain trauma, nicotine addiction, sleep apnea, autism, migraine headaches, sleep disorders, lung and sinus infections, cancer therapy with cancer drugs, nicotine addiction, and medications that cause a decrease in lung surfactants.
专利号:US-11628186-B2
优先权日:2017-02-24
标题 :Method and composition for the reduction of viral replication, duration and spread of the COVID-19 and the flu
发明人：MARTIN ALAIN
权利人:MARTIN ALAIN; CELLULAR SCIENCES INC
摘要:A method for stimulating the synthesis of nasal nitric oxide and nasal and lung surfactants to inhibit the docking and adhesion of viruses to cellular receptors, including ACE2, to reduce viral replication, duration, spread and severity of infections, and also to inhibit lung fibrosis, increase the synthesis of serotonin to reduce coughing and mouth breathing, reduce the cytokine storm produced by LI-6 caused by viruses such as COVID-19 and flu in patients susceptible to these infections, including patients with hypoxemia, asthma, chronic obstructive pulmonary disease, cystic fibrosis, diabetics, interstitial lung disease, pulmonary fibrosis, allergic rhinitis, sinusitis, smokers, sleep apnea and lung cancer, which includes: contacting mammalian cells with a therapeutically effective amount of a composition, said composition including the following constituents: sodium pyruvate; a phosphate; a salt of calcium; and a salt of magnesium.
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主要参考文献
1: Liu S, Watts AB, Du J, Bui A, Hengsawas S, Williams RO 3rd. Formulation of a novel fixed dose combination of salmeterol xinafoate and mometasone furoate for inhaled drug delivery. Eur J Pharm Biopharm. 2015 Jul 26. pii: S0939-6411(15)00317-3. doi: 10.1016/j.ejpb.2015.07.017. [Epub ahead of print] doi: 10.1016/bs.podrm.2015.02.002. Epub 2015 Apr 1. Review. doi: 10.1016/j.ijpharm.2015.05.028. Epub 2015 May 15. doi: 10.1016/j.saa.2014.08.010. Epub 2014 Aug 19. doi: 10.1016/j.saa.2014.04.158. Epub 2014 May 9. doi: 10.1517/14656566.2013.823949. Epub 2013 Jul 31. Review. doi: 10.1089/jamp.2011.0884. Epub 2011 Jun 14. doi: 10.1016/j.jsps.2010.05.001. Epub 2010 May 31.
10: Mostafapour E, Mousavi SA, Shahmiri SS, Fereshtehnejad SM. Effects of combination of fluticasone propionate and salmeterol xinafoate on lung function improvement in patients with bronchiectasis. Lijec Vjesn. 2009 Nov;131 Suppl
6:8-11.
合成参考文献
参考文献:10.1007/s00216-010-3484-3
摘要:Peters RJB, Oosterink JE, Stolker AAM, Georgakopoulos C, Nielen MWF. Generic sample preparation combined with high-resolution liquid chromatography–time-of-flight mass spectrometry for unification of urine screening in doping-control laboratories. Analytical and Bioanalytical Chemistry. 2010 Feb 16;396(7):2583–98. doi: 10.1007/s00216-010-3484-3.
参考文献:10.2165/11591730-000000000-00000
摘要:Wallerstedt SM, Brunlöf G, Sundström A. Rates of spontaneous reports of adverse drug reactions for drugs reported in children: a cross-sectional study with data from the Swedish adverse drug reaction database and the Swedish Prescribed Drug Register. Drug Saf. 2011 Aug 01;34(8):669–82. doi: 10.2165/11591730-000000000-00000.
参考文献:10.1186/1471-2466-11-40
摘要:Müller V, Gálffy G, Eszes N, Losonczy G, Bizzi A, Nicolini G, Chrystyn H, Tamási L. Asthma control in patients receiving inhaled corticosteroid and long-acting beta2-agonist fixed combinations. A real-life study comparing dry powder inhalers and a pressurized metered dose inhaler extrafine formulation. BMC Pulmonary Medicine. 2011 Jul 15;11(1):40. doi: 10.1186/1471-2466-11-40.
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