CAS: 81024-42-2; (2S)-1-[4-(2-Methoxyethyl)Phenoxy]-3-(Propan-2-Ylamino)Propan-2-Ol

该化合物是metoprologol的药用活性抗生素,一种选择性的β1-Adreneric受体阻塞剂,其立体特性增强了对心脏 β1 受体的结合性,与种族混合物相比,提高了功效并减少了离目标影响.该化合物主要用于管理高血压,心血管和心脏衰竭,因为其能够降低血压和减少心血管氧需求.(S)-抗生素展示高药效植物基因特性,包括连贯的生物利用率和可预测的代谢性,使它成为精确治疗应用的首选,其高纯度和精度特征保证临床和研究环境中的可靠性能.

结构式图片

物理性质

MSDS等安全信息

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    CAS号114218-34-7 (R)-1-O-methane... | CAS号104450-91-1 2,2'-methylened... | CAS号51384-51-1 1-[4-(2-甲氧基乙基)苯... | CAS号75-31-0 异丙胺 | CAS号105780-38-9 吡氟甲禾灵 | CAS号501-94-0 对羟基苯乙醇 | CAS号104857-48-9 1-[4-(2-羟乙基)苯氧基... | CAS号133397-54-3 (R)-3-[4-(2-Met... | CAS号56718-70-8 3-[4-(2-甲氧基乙基)苯...

    合成工艺路线路线简述

    • 75-31-0 + 105780-38-9 = 81024-42-2
      反应条件:1.1 Solvents: Isopropanol; 12 H,Rt
      标题:Asymmetric Hydrolytic Kinetic Resolution With Recyclable Polymeric Co(Iii)-Salen Complexes: A Practical Strategy In The Preparation Of (S)-Metoprolol,(S)-Toliprolol And (S)-Alprenolol: Computational Rationale For Enantioselectivity
      作者:Roy,Tamal; Et Al
      参考文献:Catalysis Science & Technology 日期:2014 卷标:4(11) 页码:3899-3908]

      95586-81-5 = 81024-42-2
      反应条件:1.1 Reagents: Potassium Carbonate Solvents: Acetone; 6 H,50 °C
      标题:Application Of Kinetic Resolution Using Hcs As Chiral Auxiliary: Novel Synthesis Of β-Blockers (S)-Betaxolol And (S)-Metoprolol
      作者:Zhang,Jing-Yu; Et Al
      参考文献:Chirality 日期:2009 卷标:21(8) 页码:745-750]

      104450-91-1 = 81024-42-2
      反应条件:1.1 Reagents: Sulfuric Acid Solvents: Methanol
      标题:A New Route From D-Mannitol To Enantiomerically Pure (S)-1-(Alkylamino)-3-(Aryloxy)-2-Propanols
      作者:Lamm,Bo; Et Al
      参考文献:Acta Chemica Scandinavica 日期:1987 卷标:41(3) 页码:202-7]

      75-31-0 = 81024-42-2
      反应条件:1.1 2 H,Reflux
      标题:Asymmetric Synthesis Of (S)-Metoprolol
      作者:Song,Guang-Wei; Et Al
      参考文献:Yingyong Huaxue 日期:2010 卷标:27(11) 页码:1286-1290]

      114218-34-7 + 75-31-0 = 81024-42-2
      反应条件:1.1 Solvents: Isopropylamine1.2 Reagents: Sulfuric Acid
      标题:A New Route From D-Mannitol To Enantiomerically Pure (S)-1-(Alkylamino)-3-(Aryloxy)-2-Propanols
      作者:Lamm,Bo; Et Al
      参考文献:Acta Chemica Scandinavica 日期:1987 卷标:41(3) 页码:202-7]

      75-31-0 + 113798-78-0 = 81024-42-2
      反应条件:1.1 Reagents: Trimethyl Orthoacetate Catalysts: Pyridinium P-Toluenesulfonate Solvents: Dichloromethane; 20 Min,Rt1.2 Reagents: Acetyl Bromide Solvents: Dichloromethane; 6 Min,Rt; 30 Min,Rt1.3 Reagents: Potassium Carbonate Solvents: Methanol; 1.5 H,Rt1.4 Solvents: Water; 1.5 H,Reflux
      标题:Asymmetric Synthesis Of (S)-Metoprolol Via Sharpless Asymmetric Dihydroxylation Induced By A Recoverable Polymer Ligand Qn-Aqn-Opeg-Ome
      作者:Cheng,Sikun; Et Al
      参考文献:Letters In Organic Chemistry 日期:2012 卷标:9(7) 页码:516-519]

      56718-70-8 + 75-31-0 = 81024-42-2
      反应条件:1.1 Catalysts: β-Cyclodextrin Solvents: Ethanol,Water1.2 -
      标题:Enantioselective Ring Opening Of Epoxides With Trimethylsilyl Azide (Tmsn3) In The Presence Of β-Cyclodextrin: An Efficient Route To 1,2-Azido Alcohols
      作者:Kamal,Ahmed; Et Al
      参考文献:Tetrahedron: Asymmetry 日期:1999 卷标:10(22) 页码:4261-4264]

      104450-90-0 + 75-31-0 = 81024-42-2
      反应条件:1.1 Solvents: Isopropylamine2.1 Reagents: Sulfuric Acid Solvents: Methanol
      标题:A New Route From D-Mannitol To Enantiomerically Pure (S)-1-(Alkylamino)-3-(Aryloxy)-2-Propanols
      作者:Lamm,Bo; Et Al
      参考文献:Acta Chemica Scandinavica 日期:1987 卷标:41(3) 页码:202-7]

      113798-78-0 = 81024-42-2
      反应条件:1.1 Reagents: Trimethyl Orthoacetate Catalysts: Pyridinium P-Toluenesulfonate Solvents: Dichloromethane; 20 Min,Rt1.2 Reagents: Acetyl Bromide; Rt; 30 Min,Rt1.3 Reagents: Potassium Carbonate Solvents: Methanol; 1.5 H,Rt1.4 Reagents: Ammonium Chloride Solvents: Water2.1 Solvents: Water; 1.5 H,Reflux
      标题:Synthesis Of (S)-Metoprolol By By Asymmetric Dihydroxylation
      作者:Xiang,Shun; Et Al
      参考文献:Hecheng Huaxue 日期:2011 卷标:19(1) 页码:127-129]

      51384-51-1 = 81024-42-2 + 81024-43-3
      反应条件:1.1 Reagents: β-Cyclodextrin,6A,6B,6C,6D,6E,6F,6G-Heptakis-O-(Carboxymethyl)-2A,2B,2C,2D,2E,2...; 20 °C
      标题:Characterization Of A Single-Isomer Carboxymethyl-Beta-Cyclodextrin In Chiral Capillary Electrophoresis
      作者:Fejos,Ida; Et Al
      参考文献:Electrophoresis 日期:2017 卷标:38(15) 页码:1869-1877]

      87-69-4 + 51384-51-1 = 81024-42-2 + 81024-43-3 [标题:Reaction Conditions
      标题:Enantioseparations Of 11 Amino Alcohols Using Di-N-Amyl L-Tartrate-Boric Acid Complex As Chiral Mobile Phase Additive By Rp-Hplc
      作者:Zou,Yanan; Et Al
      参考文献:Chromatographia 日期:2015 卷标:78(11-12) 页码:753-761]

      929205-75-4 + 75-31-0 = 81024-42-2
      反应条件:1.1 5 H,Rt
      标题:Asymmetric Synthesis Of (2S)-1-[4-(2-Methoxyethyl)Phenoxy]-3-[(1-Methylethyl)Amino]-2-Propanol [(S)-Metoprolol]
      作者:Ji,Dehua; Et Al
      参考文献:Xiandai Huagong 日期:2008 卷标:28(11) 页码:58-59]

      929205-75-4 + 75-31-0 = 81024-42-2
      反应条件:1.1 Solvents: Isopropylamine,Water; 2 H,Reflux1.2 Reagents: Ammonia Solvents: Water
      标题:Concise Synthesis Of β-Blockers (S)-Metoprolol And (S)-Betaxolol Using Hydrolytic Kinetic Resolution
      作者:Muthukrishnan,M.; Et Al
      参考文献:Tetrahedron 日期:2007 卷标:63(8) 页码:1872-1876]

      133397-54-3 + 75-31-0 = 81024-42-2
      反应条件:1.1 Catalysts: Borate(1-),Tetrafluoro-,Zinc (2:1),Hydrate; 2 H,Rt
      标题:Zinc Tetrafluoroborate Hydrate As A Mild Catalyst For Epoxide Ring Opening With Amines: Scope And Limitations Of Metal Tetrafluoroborates And Applications In The Synthesis Of Antihypertensive Drugs (Rs)/(R)/(S)-Metoprolols
      作者:Pujala,Brahmam; Et Al
      参考文献:Journal Of Organic Chemistry 日期:2011 卷标:76(21) 页码:8768-8780]

      91678-97-6 = 81024-42-2
      反应条件:1.1 Reagents: Potassium Hydroxide Solvents: Ethanol,Water; 8 - 10 H,Reflux1.2 Reagents: Acetic Acid; Neutralized
      标题:Concise Synthesis Of Two β-Adrenergic Blocking Agents In High Stereoselectivity Using The Readily Available Chiral Building Block (2S,2'S,2''S)-Tris-(2,3-Epoxypropyl)-Isocyanurate
      作者:Sonawane,Swapnil P.; Et Al
      参考文献:Organic Process Research & Development 日期:2011 卷标:15(6) 页码:1365-1370]

      149380-56-3 = 81024-42-2
      反应条件:1.1 Reagents: Hydrogen Catalysts: Platinum Dioxide Solvents: Methanol
      标题:Catalysts For Asymmetric Synthesis And Preparation Of (S)-Metoprolol
      参考文献:Japan]

      134582-18-6 = 81024-42-2
      反应条件:1.1 24 H,70 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 3
      标题:Synthesis Technique And Control Of Impurities Of (S)-Succinate Metoprolol
      作者:Di,Pan-Pan; Et Al
      参考文献:Anhui Yiyao 日期:2015 卷标:19(3) 页码:427-430]

      105780-38-9 = 81024-42-2 [标题:Reaction Conditions
      标题:Kinetic Resolution Of Aryl Glycidyl Ethers: A Practical Synthesis Of The Optically Pure β-Blocker S-Metoprolol
      作者:Gurjar,Mukund K.; Et Al
      参考文献:Heterocycles 日期:1998 卷标:48(7) 页码:1471-1476]

      56392-18-8 = 81024-42-2 [标题:Reaction Conditions
      标题:Immobilized Cellulase (Cbh I) As A Chiral Stationary Phase For Direct Resolution Of Enantiomers
      作者:Erlandsson,Per; Et Al
      参考文献:Journal Of The American Chemical Society 日期:1990 卷标:112(11) 页码:4573-4]

      104450-90-0 = 81024-42-2
      反应条件:1.1 Reagents: Sulfuric Acid Solvents: Methanol2.1 Solvents: Isopropylamine2.2 Reagents: Sulfuric Acid
      标题:A New Route From D-Mannitol To Enantiomerically Pure (S)-1-(Alkylamino)-3-(Aryloxy)-2-Propanols
      作者:Lamm,Bo; Et Al
      参考文献:Acta Chemica Scandinavica 日期:1987 卷标:41(3) 页码:202-7]

      113798-78-0 = 81024-42-2
      反应条件:1.1 Reagents: Triethylamine Solvents: Dichloromethane; Rt -> -10 °C1.2 Reagents: Thionyl Chloride Solvents: Dichloromethane; -10 °C; 4 H,-10 °C2.1 2 H,Reflux
      标题:Asymmetric Synthesis Of (S)-Metoprolol
      作者:Song,Guang-Wei; Et Al
      参考文献:Yingyong Huaxue 日期:2010 卷标:27(11) 页码:1286-1290]

      = 81024-42-2
      反应条件:1.1 Reagents: Sodium Hydride Solvents: N-Methyl-2-Pyrrolidone; 20 Min,0 - 5 °C; 5 - 6 H,5 °C -> 65 °C2.1 Reagents: Potassium Hydroxide Solvents: Ethanol,Water; 8 - 10 H,Reflux2.2 Reagents: Acetic Acid; Neutralized
      标题:Concise Synthesis Of Two β-Adrenergic Blocking Agents In High Stereoselectivity Using The Readily Available Chiral Building Block (2S,2'S,2''S)-Tris-(2,3-Epoxypropyl)-Isocyanurate
      作者:Sonawane,Swapnil P.; Et Al
      参考文献:Organic Process Research & Development 日期:2011 卷标:15(6) 页码:1365-1370
    📜对羟基苯乙醇置于(R,R) Salen Co(Iii)Oac Potassium Tert-Butylate,水,Potassium Carbonate体系中,用 N,N-二甲基乙酰胺,水,异丙醇,丁酮 作为反应溶剂,化学反应 40.0H,反应生成 美托洛尔
    参考文献:Concise Synthesis Of β-Blockers (S)-Metoprolol And (S)-Betaxolol Using Hydrolytic Kinetic Resolution
    标题:Concise Synthesis Of β-Blockers (S)-Metoprolol And (S)-Betaxolol Using Hydrolytic Kinetic Resolution
    摘要:Enantiopure (S)-Metoprolol And (S)-Betaxolol Were Prepared In An Extremely Simple And Practical Way Using Jacobsen'S Hydrolytic Kinetic Resolution Of Terminal Epoxides In Isopropanol. (C) 2007 Elsevier Ltd. All Rights Reserved.
    DOI:10.1016/j.Tet.2006.12.016

    海关参考信息

    专利信息


    专利号:US-4777293-A
    优先权日:1984-08-13
    标题 :Method for the synthesis of pharmacologically active compounds and intermediates for such synthesis
    发明人：LAMM BO R
    权利人:HAESSLE AB
    摘要:A process for the preparation of an aryloxypropanolamine of the formula n n Ar--OCH.sub.2 CH(OH)CH.sub.2 NH--R I n n wherein Ar is a carbocyclic or heterocyclic aromatic group and R is an alkyl or substituted alkyl group having 1 to 6 carbon atoms, characterized in subjecting a compound of the formula ##STR1## to oxidative cleavage to a dialdehyde of the formula ##STR2## which is then made subject to reduction, amination, acetal hydrolysis, and, where required, removal of a nitrogen protective group, to the formation of a compound of formula I, or an acid addition salt thereof, a compound of formula II and the preparation thereof from mannitol.

    专利号:US-11434195-B2
    优先权日:2017-07-20
    标题:Compositions and methods for treatment of central nervous system tumors
    发明人：SVETLOV STANISLAV IGOREVICH
    权利人:UNIV FLORIDA
    摘要:Compounds, pharmaceutical compositions, and methods for treating cancer, in particular brain cancer, are provided, including amphiphilic fatty acid/alcohol ethers (AIPs) comprising endocannabinoid and FABP motifs covalently linked to a beta-adrenoreceptor antagonist motif in one molecule. The invention includes methods for inhibiting growth of brain cancer cells by contacting the compound(s) with brain cancer cells. The invention provides a method for treating both brain cancer and brain cancer metastases, and for suppression of regrowth of brain cancer cells after radiation, surgical treatment, or chemotherapy of brain cancer. The invention also comprises an optimized chemical synthesis of the AIP compounds and methods of using the compounds, alone or in combination with another agent, for suppressing the growth of brain cancer cells, and enhancing survival of normal CNS cells, or improving recuperation from radiation, surgical or chemotherapy.

    专利号:US-5190867-A
    优先权日:1986-05-08
    标题:Process for the preparation of R-2,2-R1,R2 -1,3-dioxolane-4-methanol
    发明人：BERTOLA MAURO A; MARX ARTHUR F; KOGER HEIN S; CLAASSEN VOLKERT P; PHILLIPS GARETH T
    权利人:SHELL INTERNATIONAL PETROLEUM
    摘要:Process for the preparation of R-2,2-R 1 ,R 2 -1,3-dioxolane-4-methanol wherein R 1 and R 2 are H or alkyl groups or wherein R 1 and R 2 together with the carbon atom to which they are attached form a carbocyclic ring by subjecting a mixture of R- and S-2,2-R 1 ,R 2 -1,3-dioxolane-4-methanol to the action of a micro-organism or substances derived therefrom having the ability for stereoselective consumption of S-2,2-R 1 ,R 2 -1,3-dioxolane-4-methanol preferably until at least 80 wt % and more preferably all the S-2,2-R 1 ,R 2 -1,3-dioxolane-4-methanol is consumed. Various micro-organisms of the genus Rhodococcus, Nocardia and Corynebacterium are disclosed as suitable for the purpose. The R-isomer is a valuable intermediate for stereospecific synthesis of various biologically active compounds including S-metoprolol.

    专利号:US-2021154202-A1
    优先权日:2018-04-17
    标 题:Synthesis of dentimol, an antiglaucoma drug
    发明人：LANCINA MICHAEL; WANG JUAN; YANG HU
    权利人:UNIV VIRGINIA COMMONWEALTH
    摘要:Compounds, comprising a selective β-blocker coupled to a PAMAM dendrimer via a flexible spacer, and compositions containing the compounds, are provided. Methods of making and using the compounds and compositions for the treatment of glaucoma and other maladies are also provided.

    专利号:EP-0244912-B1
    优先权日:1986-05-08
    标 题 :A process for the preparation of r and s-2,2-r1,r2-1,3-dioxolane-4-methanol
    摘要:Process for the preparation of R-2,2-R1, R2-1,3-dioxolane-4-methanol wherein R1 and R2 are H or alkyl groups or wherein R1 and R2 together with the carbon atom to which they are attached form a carbocyclic ring by subjecting a mixture of R- and S-2,2-R1, R2-1,3-dioxolane-4-methanol to the action of a micro-organism or substances derived therefrom having the ability for stereoselective consumption of S-2,2-R1, R2-1,3-dioxolane-4-methanol preferably until at least 80 wt% and more preferably all the S-2,2-R1, R2-1,3-dioxolane-4-methanol is consumed. Various micro-organisms of the genus Rhodococcus, Nocardia and Corynebacterium are disclosed as suitable for the purpose. The R-isomer is a valuable intermediate for stereospecific synthesis of various biologically active compounds including S-metoprolol.

    专利号:US-5073639-A
    优先权日:1988-11-25
    标 题:Process for the synthesis of novel and known nitroimidazoles which are useful as sensitizing agents
    发明人：SUTO MARK J
    权利人:WARNER LAMBERT CO
    摘要:The present invention is a novel process for preparing both known and novel nitroimidazoles having novel intermediates. The process advantageously reduces the number of process steps, provides increased yield with both greater safety and greater control of stereoisomerism in the products.

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    合成参考文献


    参考文献:10.1007/bf00609683
    摘要:Dayer P, Leemann T, Marmy A, Rosenthaler J. Interindividual variation of beta-adrenoceptor blocking drugs, plasma concentration and effect: Influence of genetic status on behaviour of atenolol, bopindolol and metoprolol. European Journal of Clinical Pharmacology. 1985 Mar;28(2):149–53. doi: 10.1007/bf00609683.
    摘要:S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
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