CAS: 87333-19-5; (2S,3As,6As)-1-((S)-2-(((S)-1-Ethoxy-1-Oxo-4-Phenylbutan-2-yl)Amino)Propanoyl)Octahydrocyclopenta[b]Pyrrole-2-Carboxylic Acid

该化合物是用于通过减少外围抗药性和降低血压来治疗高血压和凝聚性心衰竭的抗抑制剂(ACE) , 其优点包括血液动力稳定性的改善,蛋白质的减少以及左心血管功能障碍患者的发病率的下降.

结构式图片

欧盟法规

ECHA物质C&L通报

上下游产品

CAS号87269-88-3 2-[N-[(S)-1-ETH... | CAS号114192-42-6 N-[(S)-1-carbet... | CAS号109428-53-7 (2S,3aS,6aS) -八... | CAS号87269-86-1 (E)-(-)-八氢环戊二烯并... | CAS号84793-24-8 N-[1-(S)-乙氧羰基-3... | CAS号82717-96-2 N-[1-(S)-乙氧羰基-3... | CAS号15121-89-8 反-3-苯甲酰丙烯酸乙酯 | CAS号87269-87-2 (S,S,S)-2-氮杂双环[... | CAS号87269-98-5 (1'S,2S)-2-(1'-... | CAS号87269-97-4 雷米普利

合成工艺路线路线简述

  • 合成目标产物 Ramipril 主要起始原料 2-[n-[(S)-1-Ethoxycarbonyl-3-Phenylpropyl]-L-Alanyl]-(1S,3S,5S)-2-Azabicyclo[3.3.0]Octane-3-Carboxylic Acid, Benzyl Ester
  • 87269-88-3 = 87333-19-5
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol
    标题:Cis,Endo-2-Azabicyclo[3.3.0]Octane-3-Carboxylic Acid Derivatives,Medicines Containing Them And Their Use
    参考文献:European Patent Organization]

    1342316-08-8 = 87333-19-5 [标题:Reaction Conditions
    标题:Highly Regio- And Enantioselective Synthesis Of γ,δ-Unsaturated Amido Esters By Catalytic Hydrogenation Of Conjugated Enamides
    作者:Gao,Min; Et Al
    参考文献:Angewandte Chemie 日期:2015 卷标:54(6) 页码:1885-1887
N-[1-(S)-乙氧羰基-3-苯丙基]-L-丙氨酸置于palladium On Activated Charcoal 氢气,三乙胺,三苯基膦体系中,用 二氯甲烷 作为反应溶剂,化学反应 7.25H,反应生成 雷米普利
参考文献:2'‐benzothiazolylthioesters Of N‐substituted Alpha Amino Acids: Versatile Intermediates For Synthesis Of Ace Inhibitors
标题:2'‐benzothiazolylthioesters Of N‐substituted Alpha Amino Acids: Versatile Intermediates For Synthesis Of Ace Inhibitors
摘要:Ace Inhibitors Have Been Synthesized From Novel Active Esters Using Simple Reaction Conditions In High Diastereomeric Selectivity. The Active Esters May Be Obtained From The Corresponding Carboxylic Acids Or Their Acid Chlorides.
DOI:10.1081/scc-200048435

海关参考信息

专利信息


专利号:US-9353057-B2
优先权日:2003-12-30
标 题:Synthesis of acyloxyalkyl carbamate prodrugs and intermediates thereof
发明人:GALLOP MARK A; DAI XUEDONG; SCHEUERMAN RANDALL A; RAILLARD STEPHEN P; MANTHATI SURESH K; YAO FENMEI; PHAN THU; LUDWIKOW MARIA; PENG GE; BHAT SEEMA
权利人:XENOPORT INC
摘要:Methods for synthesis of 1-(acyloxy)-alkyl carbamates, particularly, the synthesis of 1-(acyloxy)-alkyl carbamate prodrugs of primary or secondary amine-containing drugs are described. Also described are methods for synthesis of 1-(acyloxy)-alkyl N-hydroxysuccinimidyl carbonates which are useful intermediates in the synthesis of 1-(acyloxy)-alkyl carbamates are also described.

专利号:US-10925977-B2
优先权日:2006-10-05
标 题 :Efficient synthesis of chelators for nuclear imaging and radiotherapy: compositions and applications
发明人:YANG DAVID J; YU DONGFANG; THOMPSON ANDREW S
权利人:YANG DAVID J; YU DONGFANG; THOMPSON ANDREW S; CEIL POINT LLC; UNIV TEXAS
摘要:Novel methods of synthesis of chelator-targeting ligand conjugates, compositions comprising such conjugates, and therapeutic and diagnostic applications of such conjugates are disclosed. The compositions include chelator-targeting ligand conjugates optionally chelated to one or more metal ions. Methods of synthesizing these compositions in high purity are also presented. Also disclosed are methods of imaging, treating and diagnosing disease in a subject using these novel compositions, such as methods of imaging a tumor within a subject and methods of diagnosing myocardial ischemia.

专利号:US-10973847-B2
优先权日:2017-06-30
标题 :Core-to-surface polymerization for the synthesis of star polymers and uses thereof
发明人:JOHNSON JEREMIAH A; GOLDER MATTHEW R
权利人:MASSACHUSETTS INST TECHNOLOGY
摘要:Disclosed are methods, compositions, reagents, systems, and kits to prepare star polymers, as well as compositions and uses thereof. Various embodiments show that synthesis of these polymers contain low metal concentration to provide polymers for diverse biomedical applications including in vivo applications.

专利号:US-8445693-B2
优先权日:2008-03-20
标 题 :Catalyzed carbonylation in the synthesis of angiotensin II antagonists
发明人:CASAR ZDENKO; COPAR ANTON; CLUZEAU JEROME; PREMRL ANDREJ
权利人:CASAR ZDENKO; COPAR ANTON; CLUZEAU JEROME; PREMRL ANDREJ; LEK PHARMACEUTICALS
摘要:One embodiment disclosed in the invention is the efficient synthesis of halogenated biaryl starting material via Grignard chemistry and the use thereof. Another embodiment of the invention is the reaction of catalyzed carbonylation of the 3′-(2′-halo-biphenyl-4-ylmethyl)-1,7′-dimethyl-2′-propyl-1H,3′H-[2,5′]bibenzoimidazolyl (TLMH) using either gaseous carbon monoxide in a solvent mixture containing water; or formic acid salts optionally together with acetic acid in anhydrous solvent.

专利号:US-8263784-B2
优先权日:2008-10-30
标 题 :Method for the synthesis of a ramipril intermediate
发明人:DE LANGE BEN; HEEMSKERK DENNIS
权利人:DE LANGE BEN; HEEMSKERK DENNIS; DSM SINOCHEM PHARM NL BV
摘要:The present invention relates to a process for the preparation of octahydrocyclopenta[b]pyrrole-2-carboxylic acid and esters thereof of general formula (1) in the presence of a cobalt and/or nickel comprising catalyst and to the use of compounds of general formula (1) in the synthesis of ramipril.

专利号:US-7094920-B2
优先权日:2001-05-21
标 题 :Stereoselective synthesis of 2-hydroxy-4-phenylbutyric acid esters
发明人:TIKARE RAVEENDRA KHANDURAO
权利人:FERMENTA BIOTECH LTD
摘要:A process is described for the stereospecific preparation of an ester of formula (I): wherein * signifies the (R) stereoisomer; R 1 is selected from C 1-6 alkyl, preferably ethyl; and R 2 is hydrogen, a protecting group or a leaving group which process comprises reaction of a nitrile of formula (II): wherein * signifies the (R) stereoisonomer; and Ph is the phenyl group C 6 H 5 with a solution of an inorganic acid in an alcohol and optional conversion of the compound of formula (I) wherein R 2 is H so prepared to any other desired compound of formula (I) by standard methods in the art. The compounds of formula (I) are chiral esters, useful as intermediates in the synthesis of the family of acetylcholine esterase (ACE) inhibitors known as “prilsâ€?, such as lisinopril, cilazapril, enalapril, benazepril, ramipril, delapril, enalaprilat, imidapril, spirapril, trandolapril and others.n n*n nPh-CH 2 —CH 2 —CH(OR 2 )—COOR 1   (I)n n*n nPh-CH 2 —CH 2 —CH(H)—CN  (II)
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主要参考文献


1: Borghi C, Omboni S, Novo S, Vinereanu D, Ambrosio G, Ambrosioni E; SMILE-4 Working Party. Zofenopril and Ramipril in Combination with Acetyl Salicylic Acid in Postmyocardial Infarction Patients with Left Ventricular Systolic Dysfunction: A Retrospective Analysis of the SMILE-4 Randomized, Double-Blind Study in Diabetic Patients. Cardiovasc Ther. 2016 Apr;34(2):76-84. doi: 10.1111/1755-5922.12175. doi: 10.1016/S2213-8587(15)00368-X. Epub 2015 Oct 23. doi: 10.1016/j.tvjl.2015.10.024. Epub 2015 Oct 23. doi: 10.1155/2016/4608979. Epub 2016 Mar 6.
5: Marinšek M, Sinkovič A. Ramipril and Losartan Exert a Similar Long-Term Effect upon Markers of Heart Failure, Endogenous Fibrinolysis, and Platelet Aggregation in Survivors of ST-Elevation Myocardial Infarction: A Single Centre Randomized Trial. Biomed Res Int. 2016;2016:9040457. doi: 10.1155/2016/9040457. Epub 2016 Mar 15.
6: Simonyi G, Ferenci T. [Ramipril plus amlodipine and lisinopril plus amlodipine fixed dose combinations and patient's adherence]. Orv Hetil. 2016 Jan 3;157(1):30-4. doi: 10.1556/650.2016.30344. Hungarian. doi: 10.7326/M15-2625. Epub 2015 Nov 6. doi: 10.1111/ajt.13384. Epub 2015 Jul 14. The renin-angiotensin receptor blocker azilsartan medoxomil compared with the angiotensin-converting enzyme inhibitor ramipril in clinical trials versus routine practice: insights from the prospective EARLY registry. Trials. 2015 Dec 19;16:581. doi: 10.1186/s13063-015-1100-8.

合成参考文献


参考文献:10.4061/2011/132405
摘要:Tedla FM, Brar A, Browne R, Brown C. Hypertension in Chronic Kidney Disease: Navigating the Evidence. International Journal of Hypertension. 2011;2011():1–9. doi: 10.4061/2011/132405.
参考文献:10.4061/2011/595791
摘要:Nelson MR. Management of High Blood Pressure in Those without Overt Cardiovascular Disease Utilising Absolute Risk Scores. International Journal of Hypertension. 2011;2011():1–3. doi: 10.4061/2011/595791.
参考文献:10.1155/2011/376281
摘要:Nauli SM, Jin X, Hierck BP. The Mechanosensory Role of Primary Cilia in Vascular Hypertension. International Journal of Vascular Medicine. 2011;2011():1–9. doi: 10.1155/2011/376281.
参考文献:10.1007/s11739-011-0655-y
摘要:Silvestri E, Emmi G, D’Elios MM, Barnini T, Tamburini C. Pulmonary hemorrhage: not only vasculitis. Internal and Emergency Medicine. 2011 Jul 12;6(6):577–80. doi: 10.1007/s11739-011-0655-y.
参考文献:10.1007/s12630-011-9556-9
摘要:Forero M, Neira VM, Heikkila AJ, Paul JE. Continuous lumbar transversus abdominis plane block may spread to supraumbilical dermatomes. Journal canadien d'anesthésie. 2011 Jul 12;58(10):948. doi: 10.1007/s12630-011-9556-9.
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