CAS: 117976-89-3; 2-(((4-(3-Methoxypropoxy)-3-Methylpyridin-2-yl)Methyl)Sulfinyl)-1H-Benzo[d]Imidazole

该化合物是质子泵抑制剂(PPI),用于通过不可逆转地阻塞胃部细胞中的H+/K+ATPase酶,减少胃酸性酸生产,在临床上用于治疗胃炎复发性疾病(GERD),胃溃疡和佐林格-埃利生综合症,拉伯拉索表现出行动迅速和生物利用率高,在使用后一小时内就会发生酸抑制,其功效通过长期抑制作用保持每天一次,主要通过非酶途径代谢该化合物,与其他PPI相比,该化合物减少了药物相互作用的可能性,口服和静脉配方,为临床使用提供了灵活性.

结构式图片

欧盟法规

REACH注册ECHA物质C&L通报REACH预注册

上下游产品

CAS号117977-21-6 2-[[[4-(3-甲氧基丙氧... | CAS号1080503-70-3 2,3-dimethyl-4-... | CAS号1080503-68-9 (-)-menthyl 2-b... | CAS号924663-40-1 雷贝拉唑硫化物N-氧化物 | CAS号408332-88-7 D-(-)-tartaric ... | CAS号13811-71-7 D-酒石酸二乙酯 | CAS号937-14-4 间氯过氧苯甲酸 | CAS号924663-38-7 雷贝拉唑N-氧化物 | CAS号117976-90-6 雷贝拉唑钠

合成工艺路线路线简述

  • 合成目标产物 Rabeprazole 主要起始原料 2,3-Dimethyl-4-(3-Methoxy-Propoxy)Pyridine And 1H-Benzimidazole-2-Sulfinic Acid, (1R,2S,5R)-5-Methyl-2-(1-Methylethyl)Cyclohexyl Ester
  • (文献来源)合成步骤主要原料 2,3-Dimethyl-4-(3-Methoxy-Propoxy)Pyridine 和 1H-Benzimidazole-2-Sulfinic Acid, (1R,2S,5R)-5-Methyl-2-(1-Methylethyl)Cyclohexyl Ester
[4-(3-甲氧基丙氧基)-3-甲基-2-吡啶基]甲醇盐酸盐置于sodium Hypochlorite,氯化亚砜,Sodium Hydroxide体系中,用 乙醇,二氯甲烷,水,乙腈 用作溶剂,化学反应生成雷贝拉唑
参考文献: Process For The Preparation Of Rabeprazole[fr] Procédé Pour La Préparation De Rabéprazole
标题: Process For The Preparation Of Rabeprazole[fr] Procédé Pour La Préparation De Rabéprazole
摘要:本发明提供了iii式化合物,其制备方法以及其作为参考标记或参考标准的用途.本发明还提供了一种制备雷贝拉唑及其盐或溶剂的方法.本发明还提供了一种用于测试雷贝拉唑,其盐或溶剂纯度的色谱方法.

海关参考信息

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-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-9145368-B2
优先权日:2011-12-15
标 题 :Organocatalytic synthesis of chiral pyrazolidines and their analogues
发明人:KUMAR BOOPATHI SENTHIL; VENKATARAMASUBRAMANIAN VAITHIYANATHAN; SUDALAI ARUMUGAM
权利人:COUNCIL SCIENT IND RES
摘要:Disclosed herein is a highly enantio- (75 to 98% ee) and diastereoselective (99 to 100% de) synthesis of functionalized pyrazolidines via tandem a-amination-Corey Chaykovsky reaction of alpha unsubstituted aldehydes.

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.

专利号:US-8304409-B2
优先权日:2002-07-03
标 题:Nitrosated nonsteroidal antiinflammatory compounds, compositions and methods of use
发明人:EARL RICHARD A; EZAWA MAIKO; FANG XINQIN; GARVEY DAVID S; GASTON RICKY D; KHANAPURE SUBHASH P; LETTS L GORDON; LIN CHIA-EN; RANATUNGE RAMANI R; RICHARDSON STEWART K; SCHROEDER JOSEPH D; STEVENSON CHERI A; WEY SHIOW-JYI
权利人:EARL RICHARD A; EZAWA MAIKO; FANG XINQIN; GARVEY DAVID S; GASTON RICKY D; KHANAPURE SUBHASH P; LETTS L GORDON; LIN CHIA-EN; RANATUNGE RAMANI R; RICHARDSON STEWART K; SCHROEDER JOSEPH D; STEVENSON CHERI A; WEY SHIOW-JYI; NICOX SA
摘要:The invention describes novel nitrosated nonsteroidal antiinflammatory drugs (NSAIDs) and pharmaceutically acceptable salts thereof, and novel compositions comprising at least one nitrosated NSAID, 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 NSAID, 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 NSAID, and, optionally, at least one nitric oxide donor and/or at least one therapeutic agent. The invention also provides methods for treating inflammation, pain and fever; for treating gastrointestinal disorders; for facilitating wound healing; for treating and/or preventing gastrointestinal, renal and/or respiratory toxicities resulting from the use of nonsteroidal antiinflammatory compounds; for treating inflammatory disease states and/or disorders; and for treating and/or preventing ophthalmic diseases and/or disorders.
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主要参考文献


1: Li X, Liu S, Yu M, Xi W, Wu X, Liu D, Liu A, Wang H. Simultaneous Determination of Multiple Acid-Suppressing Drugs by UPLC-MS/MS Method and Application for Pharmacokinetics Study. Drug Des Devel Ther. 2025 Feb 11;19:955-969. doi: 10.2147/DDDT.S493911.
2: Kwon HY. So Many Choices, So Little Value: Potential Savings from Selecting Cost-Effective Proton Pump Inhibitors. Pharmacoecon Open. 2025 Feb 13. doi: 10.1007/s41669-025-00563-5. Epub ahead of print. 30(1):e70018. doi: 10.1111/hel.70018. 16(1):99240. doi: 10.5306/wjco.v16.i1.99240.
5: Ananthathandavan P, Narayanasamy D. Delineating CYP2C19-Mediated Interactions: Network Pharmacology Investigation of Ilaprazole and Clopidogrel versus Conventional Proton Pump Inhibitors. Curr Drug Discov Technol. 2024 Dec 31. doi: 10.2174/0115701638334244241224062453. Epub ahead of print.

合成参考文献


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参考文献:10.1155/2011/832414
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.
摘要:Pingili RR, Jambula MR, Ganta MR, Ghanta MR, Sajja E, Sundaram V, Boluggdu VB. Identification and synthesis of potential impurities of rabeprazole sodium. Pharmazie. 2005 Nov;60(11):814–8.
参考文献:10.1186/1471-2334-11-194
摘要:Kuntz JL, Chrischilles EA, Pendergast JF, Herwaldt LA, Polgreen PM. Incidence of and risk factors for community-associated Clostridium difficile infection: A nested case-control study. BMC Infectious Diseases. 2011 Jul 15;11(1):194. doi: 10.1186/1471-2334-11-194.
参考文献:10.3164/jcbn.10-101
摘要:Hirota K, Kudo M, Hashimoto H, Kushikata T. A marked increase in gastric fluid volume during cardiopulmonary bypass. J Clin Biochem Nutr. 2011 Jul;49(1):16–9.
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