CAS: 802904-66-1; 2-(4-Acetamido-3-((4-Chlorophenyl)Thio)-2-Methyl-1H-Indol-1-yl)Acetic Acid

该化合物是在呼吸道疾病领域的潜在治疗用途而受到调查,被归类为pestaglandin D2受体2(DP2)的选择性对抗者,在调节过敏反应和炎症方面起着重要作用;该化合物旨在抑制postaglandin D2的行动,从而有可能减少哮喘和鼻炎等症状;AZD1981,其特点是它与DP2受体的具体结合性,该受体与可能针对不同途径的其他化合物有区别;其药用基因特性,包括吸收,分布,新陈代谢和排泄,对于确定其在临床环境中的效力和安全特征至关重要;正在进行的研究旨在阐明其充分治疗潜力和任何相关的副作用,有助于发展对过敏和炎症的更有效治疗.

结构式图片

物理性质

MSDS等安全信息

上下游产品

ethyl [4-acetylamino-3-(4-chlorophenylsulfanyl)-2-methyl-1H-indol-1-yl]acetate (4-acetylamino-2-methyl-1H-indol-1-yl)acetic acid 4,4'-dichlorodiphenyl disulfide ethyl [4-(hydroxyimino)-2-methyl-4,5,6,7-tetrahydro-1H-indol-1-yl]acetate

合成工艺路线路线简述

  • 628737-12-2 + 105-36-2 = 802904-66-1
    反应条件:1.1 Reagents: Sodium Bis(Trimethylsilyl)Amide Solvents: Tetrahydrofuran2.1 Reagents: Hydrogen Catalysts: Platinum Solvents: Ethanol3.1 Reagents: Triethylamine Solvents: Dichloromethane4.1 Reagents: Sodium Hydroxide Solvents: Tetrahydrofuran,Water
    标题:Substituted Indole-1-Acetic Acids As Potent And Selective Crth2 Antagonists-Discovery Of Azd1981
    作者:Luker,Tim; Et Al
    参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2011 卷标:21(21) 页码:6288-6292]

    1142-19-4 + 3484-10-4 = 802904-66-1
    反应条件:1.1 Solvents: Ethyl Acetate2.1 Reagents: Sodium Hydride Solvents: Tetrahydrofuran2.2 Reagents: Hydrogen Catalysts: Platinum Solvents: Ethyl Acetate2.3 Reagents: Triethylamine Solvents: Dichloromethane2.4 Reagents: Ethanol,Sodium Hydroxide,Water2.5 Reagents: Hydrochloric Acid Solvents: Methyl Isobutyl Ketone
    标题:Route Design,The Foundation Of Successful Chemical Development
    作者:Cornwall,Philip; Et Al
    参考文献:Bioorganic & Medicinal Chemistry 日期:2018 卷标:26(14) 页码:4336-4347]

    25784-83-2 = 802904-66-1
    反应条件:1.1 Reagents: Triethylamine,Tert-Butyl Hypochlorite Solvents: Acetonitrile,Tetrahydrofuran; -45 °C2.1 Reagents: Sodium Hydride Solvents: Tetrahydrofuran2.2 Reagents: Hydrogen Catalysts: Platinum Solvents: Ethyl Acetate2.3 Reagents: Triethylamine Solvents: Dichloromethane2.4 Reagents: Ethanol,Sodium Hydroxide,Water2.5 Reagents: Hydrochloric Acid Solvents: Methyl Isobutyl Ketone
    标题:Route Design,The Foundation Of Successful Chemical Development
    作者:Cornwall,Philip; Et Al
    参考文献:Bioorganic & Medicinal Chemistry 日期:2018 卷标:26(14) 页码:4336-4347]

    25784-83-2 = 802904-66-1
    反应条件:1.1 Reagents: Triethylamine,Tert-Butyl Hypochlorite Solvents: Dichloromethane2.1 Reagents: Sodium Bis(Trimethylsilyl)Amide Solvents: Tetrahydrofuran3.1 Reagents: Hydrogen Catalysts: Platinum Solvents: Ethanol4.1 Reagents: Triethylamine Solvents: Dichloromethane5.1 Reagents: Sodium Hydroxide Solvents: Tetrahydrofuran,Water
    标题:Substituted Indole-1-Acetic Acids As Potent And Selective Crth2 Antagonists-Discovery Of Azd1981
    作者:Luker,Tim; Et Al
    参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2011 卷标:21(21) 页码:6288-6292]

    628737-15-5 = 802904-66-1
    反应条件:1.1 Reagents: Triethylamine Solvents: Dichloromethane2.1 Reagents: Sodium Hydroxide Solvents: Tetrahydrofuran,Water
    标题:Substituted Indole-1-Acetic Acids As Potent And Selective Crth2 Antagonists-Discovery Of Azd1981
    作者:Luker,Tim; Et Al
    参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2011 卷标:21(21) 页码:6288-6292]

    646515-19-7 = 802904-66-1
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Tetrahydrofuran,Water
    标题:Substituted Indole-1-Acetic Acids As Potent And Selective Crth2 Antagonists-Discovery Of Azd1981
    作者:Luker,Tim; Et Al
    参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2011 卷标:21(21) 页码:6288-6292]

    628737-12-2 + 105-36-2 = 802904-66-1
    反应条件:1.1 Reagents: Sodium Hydride Solvents: Tetrahydrofuran1.2 Reagents: Hydrogen Catalysts: Platinum Solvents: Ethyl Acetate1.3 Reagents: Triethylamine Solvents: Dichloromethane1.4 Reagents: Ethanol,Sodium Hydroxide,Water1.5 Reagents: Hydrochloric Acid Solvents: Methyl Isobutyl Ketone
    标题:Route Design,The Foundation Of Successful Chemical Development
    作者:Cornwall,Philip; Et Al
    参考文献:Bioorganic & Medicinal Chemistry 日期:2018 卷标:26(14) 页码:4336-4347]

    628737-13-3 = 802904-66-1
    反应条件:1.1 Reagents: Hydrogen Catalysts: Platinum Solvents: Ethanol1.2 Reagents: Triethylamine Solvents: Dichloromethane1.3 Reagents: Sodium Hydroxide Solvents: Tetrahydrofuran
    标题:Route Design,The Foundation Of Successful Chemical Development
    作者:Cornwall,Philip; Et Al
    参考文献:Bioorganic & Medicinal Chemistry 日期:2018 卷标:26(14) 页码:4336-4347]

    628737-12-2 + 105-36-2 = 802904-66-1
    反应条件:1.1 Reagents: Sodium Hydride Solvents: Tetrahydrofuran2.1 Reagents: Hydrogen Catalysts: Platinum Solvents: Ethanol2.2 Reagents: Triethylamine Solvents: Dichloromethane2.3 Reagents: Sodium Hydroxide Solvents: Tetrahydrofuran
    标题:Route Design,The Foundation Of Successful Chemical Development
    作者:Cornwall,Philip; Et Al
    参考文献:Bioorganic & Medicinal Chemistry 日期:2018 卷标:26(14) 页码:4336-4347]

    1260673-30-0 = 802904-66-1
    反应条件:1.1 Reagents: Acetic Acid,Sodium Iodide Solvents: Xylene2.1 Reagents: Sodium Hydroxide Solvents: Ethanol,Water
    标题:Route Design,The Foundation Of Successful Chemical Development
    作者:Cornwall,Philip; Et Al
    参考文献:Bioorganic & Medicinal Chemistry 日期:2018 卷标:26(14) 页码:4336-4347]

    1260673-29-7 = 802904-66-1
    反应条件:1.1 -2.1 -3.1 -4.1 Reagents: Sodium Hydroxide Solvents: Ethanol,Water
    标题:Route Design,The Foundation Of Successful Chemical Development
    作者:Cornwall,Philip; Et Al
    参考文献:Bioorganic & Medicinal Chemistry 日期:2018 卷标:26(14) 页码:4336-4347
📜4,4'-二氯二苯二硫醚置于四丁基碘化铵 水,Sodium Hydroxide体系中,用 乙醇,Xylene 作为反应溶剂,化学反应 3.67H,反应生成 4-(乙酰氨基)-3-[(4-氯苯基)硫代]-2-甲基-1H-吲哚-1-乙酸
参考文献: Intermediates And Processes For The Preparation Of 4-(Acetylamino))-3-[(4-Chloro-Phenyl) Thio]-2-Methyl-1H-Indole-1-Acetic Acid[fr] Intermédiaires Et Procédés Pour La Préparation D'Acide 4-(Acétylamino)-3-[(4-Chloro-Phényl)Thio]-2-Méthyl-1H-Indole-1-Acétique
标题: Intermediates And Processes For The Preparation Of 4-(Acetylamino))-3-[(4-Chloro-Phenyl) Thio]-2-Methyl-1H-Indole-1-Acetic Acid[fr] Intermédiaires Et Procédés Pour La Préparation D'Acide 4-(Acétylamino)-3-[(4-Chloro-Phényl)Thio]-2-Méthyl-1H-Indole-1-Acétique
摘要:这项发明涉及公式(x)的化合物及其盐,以及它们作为公式(i)的药物化合物合成改进制造过程中的中间体的用途:X为=0,=n-0H或=n-oc(o)me;y为氢,Phs-或对氯苯硫基;z为氢或-Ch2Coor1,其中r1从氢,可选择取代的烃基和可选择取代的杂环烷基中选择.

海关参考信息

专利信息


专利号:US-8227622-B2
优先权日:2009-07-06
标题:Pharmaceutical process and intermediates 714
发明人：AINGE DEBRA; MERIFIELD ERIC; THOMSON COLIN; BUTTERS MICHAEL; RAMAKRISHNAN RAVI; RAYAPATI RAVI NAIDU; SHARMA PARHALAD RAY
权利人:AINGE DEBRA; MERIFIELD ERIC; THOMSON COLIN; BUTTERS MICHAEL; RAMAKRISHNAN RAVI; RAYAPATI RAVI NAIDU; SHARMA PARHALAD RAY; ASTRAZENECA AB
摘要:The invention relates to compounds of formula (X), and salts thereof, and their use as intermediates in improved manufacturing processes for the synthesis of pharmaceutical compound (I): n n n n n n n n n n X is â• O, â• N—OH or â• N—OC(O)Me; Y is hydrogen, PhS- or p-chlorophenylsulfanyl; Z is hydrogen or —CH 2 COOR 1 wherein R 1 is selected from hydrogen, optionally substituted hydrocarbyl and optionally substituted heterocyclyl.

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主要参考文献


1: Snell N, Foster M, Vestbo J. Efficacy and safety of AZD1981, a CRTH2 receptor antagonist, in patients with moderate to severe COPD. Respir Med. 2013 Nov;107(11):1722-30. doi: 10.1016/j.rmed.2013.06.006. Epub 2013 Jul 1. doi: 10.1111/bph.12053.
3: Luker T, Bonnert R, Brough S, Cook AR, Dickinson MR, Dougall I, Logan C, Mohammed RT, Paine S, Sanganee HJ, Sargent C, Schmidt JA, Teague S, Thom S. Substituted indole-1-acetic acids as potent and selective CRTh2 antagonists-discovery of AZD1981. Bioorg Med Chem Lett. 2011 Nov 1;21(21):6288-92. doi: 10.1016/j.bmcl.2011.08.124. Epub 2011 Sep 5.

合成参考文献


摘要:S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198
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