CAS: 102625-70-7; 5-(Difluoromethoxy)-2-(((3,4-Dimethoxypyridin-2-yl)Methyl)Sulfinyl)-1H-Benzo[d]Imidazole

该化合物是一种质子泵抑制剂(PPI),主要用于治疗胃内酸再生病(GERD)和其他过度生产胃酸化的条件,其化学配方为C16H15F2N3O4S,其特点是一个硫氧化物组,一个环环和一个联氨氨氨酸味,有助于其药理活动; Pantoprazole工作,不可逆转地抑制胃肺细胞中的H+/K+ATPase酶,有效减少胃酸分泌;通常以肠胃内涂层的形式施用,以确保胃内肠道的稳定性和吸收性;该物质的特点是水中的溶性相对较低,这可能影响其生物利用率; Pantozaole一般都受到良好的调和,但潜在的副作用可能包括头痛,胃肠扰动,以及长期使用后某些感染和营养素缺乏的风险增加;其美化作用涉及快速吸收和高血压,在几小时之内发生峰值的血浆浓度.

结构式图片

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pantoprazole sulfide 5-(difluoromethoxy)-2-[[(3,4-dimethoxypyridin-2-yl-1-oxide)methyl]sulfanyl]-1H-benzoimidazole 3-methoxy-2-methyl-4-nitropyridine 1-oxide 3-methoxy-2-methylpyridin-4(1H)-onepantoprazole sodium 2-{4-[(6-(difluoromethoxy)-2-{[(3,4-dimethoxy-2-pyridyl)methyl]sulfinyl}benzimidazol-1-yl)sulfonyl]phenoxy}-N-(2-pyridyl)acetamide 2-{4-[(5-(difluoromethoxy)-2-{[(3,4-dimethoxy-2-pyridyl)methyl]sulfinyl}benzimidazol-1-yl)sulfonyl]phenoxy}-N-(2-pyridyl)acetamide 5-(difluoromethoxy)-2-[(3,4-dimethoxy-2-pyridyl)methylsulfinyl]-1H-benzimidazole

合成工艺路线路线简述

    Pantoprazole Sodium置于乙醇,水体系中,化学反应生成泮托拉唑
    参考文献: Pyridine Benzimidazole Sulfoxides With High Purity[fr] Sulfoxydes Pyridine Benzimidazole D'Une Grande Purete
    标题: Pyridine Benzimidazole Sulfoxides With High Purity[fr] Sulfoxydes Pyridine Benzimidazole D'Une Grande Purete
    摘要:一种制备具有公式(i)的吡啶苯并咪唑亚砜化合物的方法,包括使用氧化剂氧化吡啶苯并咪唑硫醚化合物的步骤,在氧化步骤中形成了一种不需要的吡啶苯并咪唑磺醇化合物作为副产物.提议在不需要的吡啶苯并咪唑磺醇产物的数量超过化合物总量的1.0%重量之前停止氧化步骤.

    专利信息


    专利号:US-5948789-A
    优先权日:1994-07-15
    标题:Process for synthesis of substituted sulphoxides
    发明人:LARSSON MAGNUS ERIK; STENHEDE URBAN JAN; SOERENSEN HENRIK; VON UNGE SVERKER PER OSKAR; COTTON HANNA KRISTINA
    权利人:ASTRA AB
    摘要:PCT No. PCT/SE95/00818 Sec. 371 Date Jul. 14, 1995 Sec. 102(e) Date Jul. 14, 1995 PCT Filed Jul. 3, 1995 PCT Pub. No. WO96/02535 PCT Pub. Date Feb. 1, 1996A novel process for enantioselective synthesis of single enantiomers of omeprazole or its alkaline salts, of other optically pure substituted 2-(2-pyridinylmethyl-sulphinyl) -1H-benzimidazoles as well as of other structurally related sulphoxides or their alkaline salts. The claimed process is an asymmetric oxidation of a pro-chiral sulphide to the single enantiomers or an enantiomerically enriched form of the corresponding sulphoxide. The application also claims the enantiomeric sulphoxide products produced by the process and their use in medicine.

    专利号:US-2015336866-A1
    优先权日:2013-01-01
    标题:Synthesis of difluoromethyl ethers and sulfides
    发明人:HARTWIG JOHN; FIER PATRICK
    权利人:UNIV CALIFORNIA
    摘要:The synthesis of difluoromethyl ethers and sulfides with a simple, non-ozone-depleting reagent is described. The difluoromethylation of phenols with this reagent occurs at room temperature within minutes with exceptional functional group tolerance. The mild conditions makes possible tandem processes for the conversion of aryl boronic acids, aryl halides and arenes to difluoromethyl ethers. Mechanistic studies support a reaction pathway involving nucleophilic attack of the phenolate to difluorocarbene.

    专利号:US-8173817-B2
    优先权日:2004-05-28
    标 题 :Stereoselective synthesis of benzimidazole sulfoxides
    发明人:REDDY BANDI PARTHASARADHI; REDDY KURA RATHNAKAR; REDDY RAPOLU RAJI; REDDY DASARI MURALIDHARA
    权利人:REDDY BANDI PARTHASARADHI; REDDY KURA RATHNAKAR; REDDY RAPOLU RAJI; REDDY DASARI MURALIDHARA; HETERO DRUGS LTD
    摘要:The present invention relates to a process for stereoselective synthesis of substituted sulfoxides either as a single enantiomer or in an enantiomerically enriched form. Thus, 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]thio]-1H-benzimidazole is reacted with (R)-camphorsulfonyl chloride to form a mixture of 1-(R)-camphorsulfonyl-5- (and 6-)methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methylthio]-1H-benzimidazole, oxidized to obtain a diastereomeric excess of 1-(R)-camphorsulfonyl-(5- and 6-)-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(S)-sulfinyl]-1H-benzimidazole over 1-(R)-camphorsulfonyl-(5- and 6-)-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(R)-sulfinyl]-1H-benzimidazole, the diastereomers are separated by fractional crystallization and the separated 1-(R)-camphorsulfonyl-(5- and 6-)-methoxy-2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl-(S)-sulfinyl]-1H-benzimidazole is deprotected to give esomeprazole.

    专利号:US-10905769-B2
    优先权日:2015-11-13
    标 题:Peptide and peptide mimetic binding antagonists of polo-like kinase 1 polo box domain and methods of use
    发明人:BURKE JR TERRENCE R; HYMEL DAVID T; TSUJI KOHEI
    权利人:THE US SECRETARY DEPARTMENT OF HEALTH & HUMAN SERVICES
    摘要:The description provides novel compounds that may serve as anticancer therapeutics. The compounds of the description bind to polo-like kinases through the polo-box domain. The peptide derivatives of the description have achieved improved efficacy in biochemical assays against Plk1. Exemplary compounds of the description include macrocyclic peptidomimetics with high affinity and selectivity for polo-like kinases, which may provide the basis for a new genre of anticancer therapeutics. Other exemplary compounds of the description include bi-valent compounds with that bind to polo-like kinases through both kinase domain and polo-box domain simultaneously by incorporating additional moieties that target Plk1 kinase domain, which significantly enhances affinitity relative and may provide the basis for a new genre of anticancer therapeutics. The description also provides methods of use, methods of preparation, compositions, and kits thereof. Further, the description provides a novel method of design and/or synthesis of phosphoryl-derived peptide derivatives useful as therapeutic agents.

    专利号:US-7211590-B2
    优先权日:2002-08-01
    标 题:Nitrosated proton pump inhibitors, compositions and methods of use
    发明人:FANG XINQIN; GARVEY DAVID S; LETTS L GORDON
    权利人:NITROMED INC
    摘要:The invention describes novel nitrosated proton pump inhibitor compounds and pharmaceutically acceptable salts thereof, and novel compositions comprising at least one nitrosated proton pump inhibitor compound, and, optionally, at least one compound that donates, transfers or releases nitric oxide, stimulates endogenous synthesis of nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor or is a substrate for nitric oxide synthase, and/or at least one therapeutic agent. The invention also provides novel compositions comprising at least one nitrosated proton pump inhibitor compound, and at least one compound that donates, transfers or releases nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor, stimulates endogenous synthesis of nitric oxide or is a substrate for nitric oxide synthase and/or at least one therapeutic agent. The invention also provides novel kits comprising at least one nitrosated proton pump inhibitor compound, and, optionally, at least one nitric oxide donor and/or at least one therapeutic agent. The invention also provides methods for treating gastrointestinal disorders; facilitating ulcer healing; decreasing the recurrence of ulcers; improving gastroprotective properties, anti-Helicobacter pylori properties or antacid properties of proton pump inhibitors; decreasing or reducing the gastrointestinal toxicity associated with the use of nonsteroidal antiinflammatory compounds; treating bacterial infections and/or viral infections.

    专利号:US-2008287407-A1
    优先权日:2003-12-10
    标题 :Nitric Oxide Releasing Pyruvate Compounds, Compositions and Methods of Use
    发明人:GARVEY DAVID S; FANG XINQIN; KHANAPURE SUBHASH P; RANATUNGA RAMANI R; WEY SHIOW-JYI
    权利人:NITROMED INC
    摘要:The invention describes novel nitrosated and/or nitrosylated pyruvate compounds and pharmaceutically acceptable salts thereof, and novel compositions comprising at least one nitrosated and/or nitrosylated pyruvate compound, and, optionally, at least one compound that donates, transfers or releases nitric oxide, stimulates endogenous synthesis of nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor or is a substrate for nitric oxide synthase, and/or at least one therapeutic agent. The invention also provides novel compositions comprising at least one pyruvate compound and at least one compound that donates, transfers or releases nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor, stimulates endogenous synthesis of nitric oxide or is a substrate for nitric oxide synthase and/or at least one therapeutic agent. The invention also provides novel kits comprising at least one pyruvate compound, that is optionally nitrosated and/or nitrosylated, and, optionally, at least one nitric oxide donor and/or at least one therapeutic agent. The invention also provides methods for treating diseases resulting from oxidative stress, diabetes, reperfusion injury following ischemia, preservation of tissues, organs, organ parts and/or limbs.
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    主要参考文献


    1: Liu H. Association between PCSK9 inhibitors and acute kidney injury: a pharmacovigilance study. Front Pharmacol. 2024 Aug 1;15:1353848. doi: 10.3389/fphar.2024.1353848.
    2: Nobre AFD, Sousa AMS, Costa ADC, Fernandes MR, Kumar R, Ponne S, Rocha MG, Rodrigues AM, Camargo ZP, Brilhante RSN. Effect of proton pump inhibitors on susceptibility and melanogenesis of Sporothrix species. J Med Microbiol. 2024 Aug;73(8). doi: 10.1099/jmm.0.001870. 29(4):e13126. doi: 10.1111/hel.13126. 76(4):3239-3244. doi: 10.1007/s12070-024-04657-0. Epub 2024 Apr 20.
    7: Sebastian A, Bhaskar E, Moorthy S, M L. Reversible Second-Degree Heart Block Attributed to Ondansetron: A Rare Side Effect. Cureus. 2024 Jul 8;16(7):e64109. doi: 10.7759/cureus.64109.

    合成参考文献


    参考文献:10.1007/s11239-010-0457-5
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    摘要:Brown SD, Connor JD, Smallwood NC, Lugo RA. Quantification of Lansoprazole in Oral Suspension by Ultra-High-Performance Liquid Chromatography Hybrid Ion-Trap Time-of-Flight Mass Spectrometry. International Journal of Analytical Chemistry. 2011;2011():1–6. doi: 10.1155/2011/832414.
    参考文献:10.1186/1752-1947-5-313
    摘要:Barrett K, Hii MW, Cade RJ. Benign gastro-colic fistula in a woman presenting with weight loss and intermittent vomiting: a case report. Journal of Medical Case Reports. 2011 Jul 14;5(1):313. doi: 10.1186/1752-1947-5-313.
    参考文献:10.1136/gut.2011.241208
    摘要:Schwarz P, Kübler JA, Strnad P, Müller K, Barth TF, Gerloff A, Feick P, Peyssonnaux C, Vaulont S, Adler G, Kulaksiz H. Hepcidin is localised in gastric parietal cells, regulates acid secretion and is induced by Helicobacter pylori infection. Gut. 2012 Feb;61(2):193–201. doi: 10.1136/gut.2011.241208.
    参考文献:10.1111/j.1523-5378.2011.00848.x
    摘要:Gu LY, Lin WW, Lu H, Chen XY, Ge ZZ, Li XB. Quadruple therapy with medications containing either rufloxacin or furazolidone as a rescue regimen in the treatment of Helicobacter pylori-infected dyspepsia patients: a randomized pilot study. Helicobacter. 2011 Aug;16(4):284–8. doi: 10.1111/j.1523-5378.2011.00848.x.
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