CAS: 80573-04-2; (E)-5-((4-((2-Carboxyethyl)Carbamoyl)Phenyl)Diazenyl)-2-Hydroxybenzoic Acid

该化合物是一种化学化合物,主要用作治疗肺炎的一种发炎性肠胃病,被归类为5-氨氨氨基二酰酸(5-SA)衍生物,通过减少结肠炎症的发炎作用,其特点是其分子配方,包括增强胃肠道稳定性和功效的diazo联系.Balsalazide通常以盐钠的形式进行施用,这能改善溶解性和吸收性.其行动机制涉及在结肠中释放5-ASA,从主题角度来说,它会抑制煽动性调解器的生产.该化合物一般具有良好的燃烧作用,副作用可能包括胃肠扰动.Balsalazide的药性皮肤病学表明,它具有低系统吸收力,可以局部地治疗调调调温素炎.总体而言,它是管理肠胃长期炎症的一个重要治疗选择.

结构式图片

合成工艺路线路线简述

  • 69-72-7 + 107-95-9 = 80573-04-2
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water; 3 H,5 °C1.2 Reagents: Hydrogen Catalysts: Palladium; 1 Atm,Rt1.3 Reagents: Hydrochloric Acid Solvents: Water; 20 Min,Rt1.4 Solvents: Water; 10 Min,Rt; Rt -> -5 °C1.5 Reagents: Sodium Nitrite Solvents: Water; 1 H,0 °C1.6 Reagents: Sodium Carbonate,Sodium Hydroxide Solvents: Water; 0 °C1.7 Reagents: Sodium Hydroxide Solvents: Water; 3 H,Ph 8,0 °C1.8 1 H,Rt
    标题:Preparation Of Sodium Balsalazide
    参考文献:China]

    62-23-7 = 80573-04-2
    反应条件:1.1 Reagents: Thionyl Chloride Solvents: Dimethylformamide; 6 H,Reflux2.1 Reagents: Sodium Hydroxide Solvents: Water; Rt -> 5 °C; 3 H,Rt2.2 Reagents: Hydrochloric Acid Solvents: Water; 1 H,Rt3.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol; 8 H,65 °C4.1 Reagents: 4-Nitrobenzoic Acid,Hydrochloric Acid Solvents: Water; 1 H,0 °C4.2 Reagents: Sodium Carbonate,Sodium Hydroxide Solvents: Water; 0 °C4.3 Reagents: Sodium Hydroxide Solvents: Water; 3 H,Ph 84.4 Reagents: Hydrochloric Acid Solvents: Water; 1 H
    标题:Synthesis Of Balsalazide Sodium
    作者:Shi,Zhenhua; Et Al
    参考文献:Zhongguo Yiyao Gongye Zazhi 日期:2003 卷标:34(11) 页码:537-538]

    59642-21-6 = 80573-04-2
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol; 3 H,1 Bar,Rt2.1 Reagents: Sodium Carbonate,Sodium Hydroxide Solvents: Water; 15 - 20 Min,0 °C2.2 Reagents: Sodium Hydroxide Solvents: Water; 3 H,Ph 10,0 °C2.3 Reagents: Hydrochloric Acid Solvents: Water; Ph 1
    标题:Sustainable Synthesis Of Balsalazide And Sulfasalazine Based On Diazotization With Low Concentrations Of Nitrogen Dioxide In Air
    作者:Hofmann,Dagmar; Et Al
    参考文献:Chemistry - A European Journal 日期:2017 卷标:23(17) 页码:4042-4045]

    107-95-9 = 80573-04-2
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water; 30 Min,0 °C; 2 H,0 °C -> Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 2 - 3,0 °C2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol; 3 H,1 Bar,Rt3.1 Reagents: Sodium Carbonate,Sodium Hydroxide Solvents: Water; 15 - 20 Min,0 °C3.2 Reagents: Sodium Hydroxide Solvents: Water; 3 H,Ph 10,0 °C3.3 Reagents: Hydrochloric Acid Solvents: Water; Ph 1
    标题:Sustainable Synthesis Of Balsalazide And Sulfasalazine Based On Diazotization With Low Concentrations Of Nitrogen Dioxide In Air
    作者:Hofmann,Dagmar; Et Al
    参考文献:Chemistry - A European Journal 日期:2017 卷标:23(17) 页码:4042-4045

海关参考信息

专利信息


专利号:US-7411031-B2
优先权日:2001-11-23
标 题 :Synthesis of polyanhydrides
发明人:UHRICH KATHRYN E; SCHMELTZER ROBERT C; ANASTASIOU THEODORE JAMES
权利人:UNIV RUTGERS
摘要:The present invention provides a method for forming compounds of Formulan nHO—C(â•?O)R 1 —X—R 2 —X—R 1 —C(â•?O)—O—Hn nwherein compound (I) can be polymerized to provide a polymer that contains therapeutically active compounds. In the compounds of the invention, each R 1 is group that will provide the therapeutically active compound upon hydrolysis of the polymer; each X is independently an ester linkage or an amide linkage; and R 2 is a linking group.

专利号:US-8754197-B2
优先权日:2004-07-07
标题:Synthesis of azo bonded immunoregulatory compounds
发明人:RIGGS-SAUTHIER JENNIFER A; EKWURIBE NNOCHIRI N
权利人:RIGGS-SAUTHIER JENNIFER A; EKWURIBE NNOCHIRI N; BIOCON LTD
摘要:Methods are disclosed for preparing compounds of Formula I: n nwhere R 1 , R 3 , and R 4 are independently hydrogen or C 1 to C 4 alkyl, and R 2 is:n n nwhere R 5 is selected from the group consisting of hydrogen and C 1 to C 4 alkyl, orn n nwhere R 6 , R 7 and R 8 are independently hydrogen or C 1 to C 4 alkyl; or the esters or pharmacologically acceptable salts thereof. The compounds and or their metabolites can be used to treat or prevent various diseases, particularly inflammatory conditions of the GI tract.

专利号:US-11993606-B2
优先权日:2015-10-16
标题:Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof
发明人:MOHAMED MOHAMED-ESLAM F; OTHMAN AHMED A; PANGAN AILEEN L; SONG IN-HO; KLÜNDER BEN; VOSS JEFFREY W; PADLEY ROBERT J; CAMP HEIDI S
权利人:ABBVIE INC
摘要:The present disclosure relates to processes for preparing (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide, solid state forms thereof, and corresponding pharmaceutical compositions, methods of treatment (including treatment of rheumatoid arthritis and various spondyloarthritic conditions, including types of axial spondyloarthritis (axSpA)), kits, methods of synthesis, and products-by-process. In various aspects, provided are methods for treating active non-radiographic axSpA (nr-axSpA) and methods for treating active ankylosing spondylitis (AS).

专利号:US-11857778-B2
优先权日:2018-01-17
标 题:Systems and methods for treating inflammatory bowel disease through peripheral nerve stimulation
发明人:HAMNER SAMUEL RICHARD; ROSS ERIKA KRISTINE; ROSENBLUTH KATHRYN H
权利人:CALA HEALTH INC
摘要:Systems and methods for treating symptoms of an inflammatory gastrointestinal disease in a patient with transcutaneous stimulation of a peripheral nerve are disclosed. The method can include any number of positioning a first peripheral nerve effector on the patient's skin to stimulate the peripheral nerve of the patient, delivering a first electrical nerve stimulation signal transcutaneously to the peripheral nerve through the first peripheral nerve effector, and modifying at least one brain or spinal cord autonomic feedback loop relating to release of neurotransmitters from the autonomic nervous system that modulate synthesis of inflammatory biomarkers and reduce inflammation relating to the inflammatory gastrointestinal disease.

专利号:US-11976077-B2
优先权日:2015-10-16
标 题 :Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-α]pyrrolo[2,3-e]-pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms therof
发明人:PANGAN AILEEN L; TEIXEIRA HENRIQUE D; MOHAMED MOHAMED-ESLAM F; OTHMAN AHMED A; KLÜNDER BEN; VOSS JEFFREY W; PADLEY ROBERT J; CAMP HEIDI S
权利人:ABBVIE INC
摘要:The present disclosure relates to processes for preparing (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide, solid state forms thereof, and corresponding pharmaceutical compositions, methods of treatment (including treatment of rheumatoid arthritis and atopic dermatitis), kits, methods of synthesis, and products-by-process.

专利号:US-11512092-B2
优先权日:2015-10-16
标题 :Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]-pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof
发明人:ALLIAN AYMAN; JAYANTH JAYANTHY; MOHAMED MOHAMED-ESLAM F; MULHERN MATHEW; NORDSTROM FREDRIK LARS; OTHMAN AHMED A; ROZEMA MICHAEL J; BHAGAVATULA LAKSHMI; MARROUM PATRICK J; MAYER PETER T; SHEIKH AHMAD Y; BORCHARDT THOMAS B; KLÜNDER BEN
权利人:ABBVIE INC
摘要:The present disclosure relates to processes for preparing (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide, solid state forms thereof, and corresponding pharmaceutical compositions, methods of treatment (including treatment of rheumatoid arthritis and various spondyloarthritic conditions, including types of axial spondyloarthritis (axSpA)), kits, methods of synthesis, and products-by-process. In various aspects, provided are methods for treating active non-radiographic axSpA (nr-axSpA) and methods for treating active ankylosing spondylitis (AS).
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主要参考文献


1: Kim SL, Kim SH, Park YR, Liu YC, Kim EM, Jeong HJ, Kim YN, Seo SY, Kim IH, Lee SO, Lee ST, Kim SW. Combined Parthenolide and Balsalazide Have Enhanced Antitumor Efficacy Through Blockade of NF-κB Activation. Mol Cancer Res. 2017 Feb;15(2):141-151. doi: 10.1158/1541-7786.MCR-16-0101. Epub 2016 Nov 14. doi: 10.1002/chem.201605359. Epub 2017 Jan 25. doi: 10.1002/14651858.CD000544.pub4. Review. doi: 10.1111/jgh.13280. doi: 10.5217/ir.2015.13.3.233. Epub 2015 Jun 9.
6: Sousa T, Yadav V, Zann V, Borde A, Abrahamsson B, Basit AW. On the colonic bacterial metabolism of azo-bonded prodrugsof 5-aminosalicylic acid. J Pharm Sci. 2014 Oct;103(10):3171-5. doi: 10.1002/jps.24103. Epub 2014 Aug 4. doi: 10.3748/wjg.v20.i13.3564. Review.
8: Coman RM, Glover SC, Gjymishka A. Febrile pleuropericarditis, a potentially life-threatening adverse event of balsalazide--case report and literature review of the side effects of 5-aminosalicylates. Expert Rev Clin Immunol. 2014 May;10(5):667-75. doi: 10.1586/1744666X.2014.902313. Epub 2014 Apr 1. Review. doi: 10.1007/s00228-014-1660-7. Epub 2014 Mar 11.

合成参考文献


摘要:British Medical Journal., 320(613), 2000 []
参考文献:10.1021/jm010852p
摘要:Carceller E, Salas J, Merlos M, Giral M, Ferrando R, Escamilla I, Ramis J, García-Rafanell J, Forn J. Novel azo derivatives as prodrugs of 5-aminosalicylic acid and amino derivatives with potent platelet activating factor antagonist activity. J Med Chem. 2001 Aug 30;44(18):3001–13. doi: 10.1021/jm010852p.
参考文献:10.1111/j.1365-2036.2004.01964.x
摘要:Sandborn WJ, Hanauer SB, Buch A. Comparative pharmacokinetics of equimolar doses of 5-aminosalicylate administered as oral mesalamine (Asacol) and balsalazide: a randomized, single-dose, crossover study in healthy volunteers. Aliment Pharmacol Ther. 2004 May 15;19(10):1089–98. doi: 10.1111/j.1365-2036.2004.01964.x.
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