CAS: 94497-51-5; 4-((5,5,8,8-Tetramethyl-5,6,7,8-Tetrahydronaphthalen-2-yl)Carbamoyl)Benzoic Acid

该化合物是合成的视网膜,主要以其在治疗急性球球球细胞白血病(APL)时的应用而闻名.它作为有选择性的抗体,特别是RAR,在管理细胞分化和扩散所涉基因表达方面起着关键作用.塔米巴罗坦对这些受体表现出高度亲近性,促进将球球球细胞编成成熟的颗粒细胞,从而帮助处理杀伤人员地雷.该化合物的特点是它能够调节各种生物途径,包括流行病和细胞循环调节.在物理特性方面,塔米巴罗坦通常被作为白色到非白色晶状粉,有机溶剂中含有中溶性,水溶性有限.其药理学学涉及口服管理,具有有利的吸收特征.与许多再生类相比,潜在的副作用可能包括皮肤相关反应和致畸效应,因此需要在治疗期间仔细监测.

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物理性质

MSDS等安全信息

上下游产品

CAS号94497-53-7 4-((5,5,8,8-四甲基... | CAS号110-03-2 2,5-二甲基-2,5-己二醇 | CAS号6223-78-5 2,5-二氯-2,5-二甲基己烷 | CAS号6683-46-1 1,1,4,4-四甲基-1,2... | CAS号102121-55-1 1,1,4,4-四甲基-6-硝... | CAS号92050-16-3 5,6,7,8-四氢-5,5,... | CAS号94497-53-7 4-((5,5,8,8-四甲基...

合成工艺路线路线简述

  • 合成目标产物 Tamibarotene 主要起始原料 Methyl 4-((5,5,8,8-Tetramethyl-5,6,7,8-Tetrahydronaphthalen-2-yl)Carbamoyl)Benzoate
  • 94497-53-7 = 94497-51-5
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Methanol,Water; 1 H,Reflux1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 2.5,Cooled
    标题:Improved Synthesis Of Anti-Leukemia Drug Tamibarotene
    作者:Xiao,Jian; Luo,Lan; He,Shulan
    参考文献:Zhongguo Yaowu Huaxue Zazhi 日期:2009 卷标:19(4) 页码:268-269]

    94497-53-7 = 94497-51-5
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Methanol,Water; 1 H,30 - 40 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 3 - 4
    标题:New Process For Preparation Of Tamibarotene
    参考文献:China]

    1446134-13-9 = 94497-51-5
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Methanol,Water; 3 H,80 °C; 80 °C -> Rt
    标题:Highly Efficient Aminocarbonylation Of Iodoarenes At Atmospheric Pressure Catalyzed By A Robust Acenaphthoimidazolyidene Allylic Palladium Complex
    作者:Fang,Weiwei; Deng,Qinyue; Xu,Mizhi; Tu,Tao
    参考文献:Organic Letters 日期:2013 卷标:15(14) 页码:3678-3681]

    94497-53-7 = 94497-51-5
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Methanol,Water; 3 H,Rt -> Reflux; Reflux -> Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 4,Rt
    标题:Preparation Of N1-(6-(Hydroxamino)-6-Oxohexyl)-N4-(5,5,8,8-Tetramethyl-5,6,7,8-Tetrahydro-2-Naphthyl) Terephthalamide As Histone Deacetylase Inhibitor For Treating Cancer
    参考文献:China]

    1679-64-7 + 92050-16-3 = 94497-51-5
    反应条件:1.1 Reagents: Oxalyl Chloride Catalysts: Dimethylformamide Solvents: Ethyl Acetate; < 30 °C; 8 H,60 °C1.2 Solvents: Ethyl Acetate; 40 Min,< 20 °C1.3 Reagents: Triethylamine; < 20 °C; 3.5 H,Rt1.4 Reagents: Hydrochloric Acid Solvents: Water; 30 Min,Rt1.5 Reagents: Sodium Hydroxide Solvents: Ethanol; 3 H,60 °C1.6 Reagents: Sulfuric Acid Solvents: Ethanol,Water; Ph 2
    标题:Synthesis Of Tamibarotene Via Ullmann-Type Coupling
    作者:Bao,Xuefei; Qiao,Xuejun; Bao,Changshun; Liu,Yuting; Zhao,Xuan; Et Al
    参考文献:Organic Process Research & Development 日期:2017 卷标:21(5) 页码:748-753]

    34231-49-7 + 92050-16-3 = 94497-51-5
    反应条件:1.1 Catalysts: Trifluoromethanesulfonic Acid,Potassium Iodide Solvents: Toluene; 24 H,150 °C
    标题:Highly Chemoselective Transamidation Of Unactivated Tertiary Amides By Electrophilic N-C(O) Activation By Amide-To-Acyl Iodide Re-Routing
    作者:Zuo,Dongxu; Wang,Qun; Liu,Long; Huang,Tianzeng; Szostak,Michal; Et Al
    参考文献:Angewandte Chemie 日期:2022 卷标:61(24)]

    94497-53-7 = 94497-51-5
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water
    标题:Retinobenzoic Acids. 1. Structure-Activity Relationships Of Aromatic Amides With Retinoidal Activity
    作者:Kagechika,Hiroyuki; Kawachi,Emiko; Hashimoto,Yuichi; Shudo,Koichi; Himi,Toshiyuki
    参考文献:Journal Of Medicinal Chemistry 日期:1988 卷标:31(11) 页码:2182-92]

    = 94497-51-5 [标题:Reaction Conditions
    标题:Design,Synthesis And Biological Evaluation Of Novel Tamibarotene Derivative As Multitarget Anticancer Agent
    作者:Jiang,Yuqi; Hou,Jinning; Li,Xiaoyang; Xu,Wenfang; Zhang,Yingjie
    参考文献:Letters In Drug Design & Discovery 日期:2016 卷标:13(8) 页码:729-733]

    = 94497-51-5 [标题:Reaction Conditions
    标题:A New Method For Preparing Tamibarotene Key Intermediate 5,5,8,8-Tetramethyl-5,6,7,8-Tetrahydro-2-Naphthylamine
    参考文献:China]

    = 94497-51-5 [标题:Reaction Conditions
    标题:Tamibarotene: Leukemia Therapy Retinoid Rarα Agonist
    作者:Davies,S. L.; Castaner,J.; Garcia-Capdevila,L.
    参考文献:Drugs Of The Future 日期:2005 卷标:30(7) 页码:688-693]

    94497-53-7 = 94497-51-5
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Methanol1.2 Reagents: Hydrochloric Acid Solvents: Water
    标题:Preparation Of 4-[(5,6,7,8-Tetrahydro-5,6,8,8-Terramethyl-2-Naphthalenyl)Carbamoyl]Benzoic Acid Derivatives
    参考文献:World Intellectual Property Organization]

    1446134-13-9 = 94497-51-5
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Methanol,Water; 3 H,Reflux; Reflux -> Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 3
    标题:Method For Synthesizing Tamibarotene Using Acenaphthoimidazole N-Heterocyclic Carbene Allyl Palladium Chloride As Catalyst
    参考文献:China]

    94497-53-7 = 94497-51-5
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Methanol,Water; 3 H,Reflux; Reflux -> Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 4
    标题:Tamibarotene-Cinnamic Hydroxamic Acid Derivative As Histone Deacetylase Inhibitor And Its Preparation,Pharmaceutical Compositions And Use In The Treatment Of Cancer
    参考文献:China]

    94497-53-7 = 94497-51-5
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Methanol,Water; Heated
    标题:Process Improvement Of Tamibarotene Preparation
    作者:Zhao,Ming-Zhu; Zang,Cheng-Xu; Cai,Zhan; Jiang,Zhi-Hui; Huang,Jing-Hua; Et Al
    参考文献:Yaoxue Shijian Zazhi 日期:2012 卷标:30(4) 页码:287-288]

    94497-53-7 = 94497-51-5
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Methanol,Water; Rt -> Reflux; 1 H,Reflux; Reflux -> Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 4.0
    标题:Synthesis Of Tamibarotene
    作者:Bian,Haiyong; Xu,Wenfang
    参考文献:Zhongguo Yiyao Gongye Zazhi 日期:2009 卷标:40(1) 页码:9-11]

    94497-53-7 = 94497-51-5
    反应条件:1.1 Reagents: Potassium Carbonate Solvents: Water; 30 Min,Reflux; Cooled1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 2
    标题:Process For Synthesizing Tamibarotene
    参考文献:China]

    94497-53-7 = 94497-51-5
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Methanol
    标题:Method For Synthesizing Tamibarotene
    参考文献:China]

    = 94497-51-5 [标题:Reaction Conditions
    标题:Synthesis Of Am80 (Tamibarotene) Prodrug Candidates,Congeners And Metabolites
    作者:Muratake,Hideaki; Amano,Yohei; Toda,Takahiro; Sugiyama,Kiyoshi; Shudo,Koichi
    参考文献:Chemical & Pharmaceutical Bulletin 日期:2013 卷标:61(8) 页码:846-852]

    = 94497-51-5 [标题:Reaction Conditions
    标题:Method For Preparing Tamibarotene With Stable Crystal Form
    参考文献:China]

    = 94497-51-5 [标题:Reaction Conditions
    标题:Method For Synthesizing 5,6,7,8-Tetrahydro-5,5,8,8-Tetramethyl-2-Naphthylamine
    参考文献:China
📜4-((5,5,8,8-四甲基-5,6,7,8-四氢萘-2-基)氨基甲酰基)苯甲酸甲酯置于sodium Hydroxide体系中,用 乙醇 作为反应溶剂,化学反应生成 他米巴罗汀
参考文献:视黄苯甲酸.1.芳族酰胺与类视色素活性的结构-活性关系.
标题:视黄苯甲酸.1.芳族酰胺与类视色素活性的结构-活性关系.
摘要:已显示两种类型的芳族酰胺,对苯二甲酸单苯胺和(芳基甲酰胺基)苯甲酸具有有效的类维生素a活性,可以归类为类维生素a.基于对人早幼粒细胞白血病细胞hl-60的分化诱导活性,讨论了这些酰胺的构效关系.在通式4(x = Nhco或conh)中,引起类视色素活性的必要因素是在其间位的中等尺寸烷基(异丙基,叔丁基等)和在其对位的羧基.另一个苯环.酰胺结构的键可以颠倒,该部分显然具有将两个苯环相对于彼此定位在适当位置的作用.推测是由于所得的构象变化,在酰胺基邻位的环位置取代或酰胺基的n-甲基化导致活性降低.显然,苄基甲基和羧基的相互取向以及它们之间的距离是决定类视色素活性的必要因素.在合成的化合物中,4-[((5,6,7,8-四氢-5,5,8,8-四甲基-2-萘基)氨基甲酰基]苯甲酸(am80)和4-[(5,6,在该测定中,7,8-四氢-5,5,8,8-四甲基-2-萘基[羧酰胺基]苯甲酸(am580)的
DOI:10.1021/jm00119A021

海关参考信息

专利信息


专利号:US-6521814-B1
优先权日:1997-12-22
标题:Use of ligands for treatment of diseases responsive to retinoids
发明人：CHAMBON PIERRE; BORRELLI EMILIANA; GHYSELINCK NORBERT B; DUPE VALERIE; MARK MANUEL; METZGER DANIEL
权利人:INST NAT SANTA ET DE LA RECH M; CENTRE NAT RECH SCIENT; UNIV PASTEUR; BRISTOL MYERS SQUIBB CO
摘要:The invention relates to methods for treatment of neurological disease by administering an agent which interacts with a retinoid receptor associated with the neurological disease. The invention is also related to a method of modulating dopamine receptor synthesis by introducing an agent that interacts with a retinoid receptor associated with the dopamine receptor synthesis. The invention is further related to a transgenic animal, e.g., mouse, and mammalian cell line, which is deficient in the normal synthesis of one or more receptors of RARα, β, γ and RXR, and cell line thereof.

专利号:WO-2019182527-A1
优先权日:2018-03-21
标 题:Methyl jasmonate derivatives as possible drug candidates for use in treatment of cancer
发明人：GUZEL MUSTAFA; OZDATLI SUKRAN; SAVLUG OZGECAN; SUCU BILGESU ONUR
权利人:T C ISTANBUL MEDIPOL UNIV
摘要:The present invention relates to the active methyl jasmonate analogues which are effective on the cancer disease and / or on the mechanisms that constitute the disease, the methods of synthesis of said analogs / derivatives and their use in the treatment of a variety of diseases, particularly for treatment of cancer and cancer-causing diseases.

专利号:US-2022118123-A1
优先权日:2019-02-22
标 题 :Combination of ar antagonists and targeted thorium conjugates
发明人：HAMMER STEFANIE; HAGEMANN URS BEAT; HAENDLER BERNARD; LEJEUNE PASCALE; ZITZMANN-KOLBE SABINE; SCHATZ CHRISTOPH; KARLSSON JENNY
权利人:BAYER AG; BAYER AS
摘要:The present invention covers combinations of at least two components, component A and component B, comprising component A being PSMA-TTC, and component B being an antiandrogen selected form AR antagonists such as from cyproterone acetate, bicalutamide, flutamide, nilutamide, enzalutamide, apalutamide, darolutamide or keto-darolutamide, or an AR degrader such as ARV-110, or an ARN-terminal domain binder such as EPI-506, or an antisense oligonucleotide that reduces AR expression such as EZN-4176 or AZD-5312, or an androgen synthesis inhibitor such as abiraterone, particularly abiraterone acetate, seviteronel, galeterone, orteronel or ketoconazole, or a dual AR antagonist and androgen synthesis inhibitor such as ODM-204. Another aspect of the present invention covers the use of such combinations as described herein for the preparation of a medicament for the treatment or prophylaxis of a disease, particularly for the treatment of a hyper-proliferative disease.

专利号:US-2006263340-A1
优先权日:2005-04-29
标题 :Treating gastrointestinal diseases with modulators of retinoic acid
发明人：ANDRIAN ULRICH H V; MORA RODRIGO
权利人:ANDRIAN ULRICH H V; MORA RODRIGO
摘要:T cells are programmed to target the gastrointestinal tract by activation with dendritic cells capable of producing and/or transporting retinoic acid. Methods for using the programmed dendritic cells and/or T and/or B cells to treat a variety of pathogens and infectious agents residing in the intestine are also disclosed. Similarly, inhibitors of retinoic acid synthesis by dendritic cells or other cells in the gut, and inhibitors of retinoic acid receptors in T and/or B cells or other cells in the intestinal mucosa, are disclosed for treating a variety of gastrointestinal autoimmune diseases such as inflammatory bowel disease and celiac disease.

专利号:US-8742045-B2
优先权日:2009-06-03
标题:Polymerization initiator for living radical polymerization
发明人：GOTO ATSUSHI; KIM JEONG SIK; TSUJII YOSHINOBU; FUKUDA TAKESHI
权利人:GOTO ATSUSHI; KIM JEONG SIK; TSUJII YOSHINOBU; FUKUDA TAKESHI; UNIV KYOTO
摘要:Provided is a method of living radical polymerization which does not necessitate complicated and intricate synthesis of a dormant species and which is highly efficient. A halogenated derivative compound is used as a dormant species for initiating living radical polymerization. The derivative compound is obtained by halogenating an alcohol compound having a non-conjugated structure or an amine compound having a non-conjugated structure with a halogenating agent capable of halogenating an alcohol or amine. A radical produced by elimination of halogen from the halogenated derivative compound is allowed to react with the unsaturated bond of the monomer. Thus, the monomer, which has a radical-reactive unsaturated bond, is polymerized by living radical polymerization. Preferably, the halogenating agent is a compound (NIS or the like) which also has a function as a catalyst.

专利号:US-2021002209-A1
优先权日:2018-02-13
标题 :Novel crystalline forms of tamibarotene for treatment of cancer
发明人：HANNA MAZEN; PERERA MANOMI; YAN JIYU; HANNA ANDREW
权利人:TRANSGENEX NANOBIOTECH INC
摘要:Synthesis and characterization of novel tamibarotene forms suitable for pharmaceutical compositions in drug delivery systems to treat human or warm-blooded mammal diseases.

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主要参考文献


1: Goulding E, Ward L, Allan F, Dittman D, Salcedo-Sora JE, Carnell AJ. Development of the esterase PestE for amide bond synthesis under aqueous conditions: Enzyme cascades for converting waste PET into tamibarotene. Angew Chem Int Ed Engl. 2024 Oct
28:e202414162. doi: 10.1002/anie.202414162. Epub ahead of print. 63(42):e202410616. doi: 10.1002/anie.202410616. Epub 2024 Sep 5.
265:110301. doi: 10.1016/j.clim.2024.110301. Epub 2024 Jun 27. 103(26):e38690. doi: 10.1097/MD.0000000000038690.

合成参考文献


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参考文献:10.1532/ijh97.05056
摘要:Naito K, Kobayashi M, Sahara N, Shigeno K, Nakamura S, Shinjo K, Tobita TD, Takeshita A, Ohno R, Ohnishi K. Two Cases of Acute Promyelocytic Leukemia Complicated by Torsade de Pointes during Arsenic Trioxide Therapy. International Journal of Hematology. 2006 May 01;83(4):318–23. doi: 10.1532/ijh97.05056.
参考文献:10.1016/j.cellimm.2011.05.005
摘要:Morohoshi K, Yoshida K, Nakagawa Y, Hoshikawa S, Ozaki H, Takahashi Y, Ito S, Mori K. Effects of synthetic retinoid Am80 on iodide-induced autoimmune thyroiditis in nonobese diabetic mice. Cell Immunol. 2011;270(1):1–4. doi: 10.1016/j.cellimm.2011.05.005.
参考文献:10.1182/blood-2012-06-436022
摘要:Ding W, Shimada H, Li L, Mittal R, Zhang X, Shudo K, He Q, Prasadarao NV, Wu L. Retinoid agonist Am80-enhanced neutrophil bactericidal activity arising from granulopoiesis in vitro and in a neutropenic mouse model. Blood. 2013 Feb 07;121(6):996–1007.
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