(R)-(1-Naphthalen-1-Yl-Ethyl)-[3-(3-Trifluoromethyl-Phenyl)-Allyl]-Amine置于5%-Palladium/activated Carbon 氢气体系中,用 甲苯 用作溶剂,10.0~30.0 °C,152.0 Kpa 条件下,以79.4%的收率获得西那卡塞 参考文献: A Process For The Synthesis Of Cinacalcet Hydrochloride[fr] Procédé Pour La Synthèse De Chlorhydrate De Cinacalcet 标题: A Process For The Synthesis Of Cinacalcet Hydrochloride[fr] Procédé Pour La Synthèse De Chlorhydrate De Cinacalcet 摘要:描述了一种用于制备盐酸西那卡塞的过程,包括以下步骤:A)将(R)-(+)-1-(1-萘基)乙胺(II)与3-[3-(三氟甲基)苯基]丙烯醛(III)反应,得到非隔离的中间体(R)-N-[3-[3-(三氟甲基)苯基]-2-丙烯基亚胺-N-[1-(1-萘基)乙胺(Iv);B)用顺序加入的方式还原非隔离的中间体(R)-N-[3-[3-(三氟甲基)苯基]-2-丙烯基亚胺-N-[1-(1-萘基)乙胺(Iv),包括:-氢硼酸钠,甲醇和碱的溶液,-草酸和-碱,以获得(R)-N-[3-[3-(三氟甲基)苯基]-2-丙烯基]-1-(1-萘基)乙胺(V),在加入草酸后通过沉淀化合物(V)的草酸盐而得到;C)氢化(R)-N-[3-[3-(三氟甲基)苯基]-2-丙烯基]-1-(1-萘基)乙胺(V),从而获得(R)-N-(3-(3-(三氟甲基)苯基)丙基)-1-(1-萘基)乙胺西那卡塞碱(Vi),在乙酸乙酯中重新提取;D)用盐酸处理乙酸乙酯中的西那卡塞碱(Vi)溶液,得到盐酸西那卡塞(I).
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-8614354-B2 优先权日:2008-06-18 标题 :Process for the synthesis of cinacalcet hydrochloride 发明人:FERRARI MASSIMO; GHEZZI MARCELLO; BONALDI MATTEO 权利人:FERRARI MASSIMO; GHEZZI MARCELLO; BONALDI MATTEO; ERREGIERRE SPA 摘要:There is described a process for the preparation of cinacalcet hydrochloride (I) which includes the steps of: a) reacting (R)-(+)-1-(1-naphthyl)ethylamine (II) with 3-[3-(trifluoromethyl)phenyl]propenaldehyde (III) to afford the non isolated intermediate (R)—N-[3-[3-(trifluoromethyl)phenyl]-2-propenylimino-N-[1-(1-naphthyl)ethylamine (IV); b) reducing the non isolated intermediate (R)—N-[3-[3-(trifluoromethyl)phenyl]-2-propenylimino-N-[-1-(1-naphthyl)ethylamine (IV) with a sequential addition of:—a solution of sodium borohydride, methanol and a base,—oxalic acid and—a base to obtain (R)—N-[3-[3-(tifluoromethyl)phenyl]-2-propenyl]-1-(1-naphthyl)ethylamine (V) by passing through the precipitation of the oxalate salt of compound (V) after the addition of oxalic acid; c) hydrogenating (R)—N-[3-[3-(trifluoromethyl)phenyl]-2-propenyl]-1-(1-naphthyl)ethylamine (V) thus obtaining (R)—N-(3-(3-(trifluoromethyl)phenyl]propyl]-1-(1-naphthyl)ethylamine cinacalcet base (VI), which is retaken in ethyl acetate; and d) treating the solution of cinacalcet base (VI) in ethyl acetate with hydrochloric acid to afford cinacalcet hydrochloride (I).
专利号:WO-2025099741-A1 优先权日:2023-11-07 标题:Process for the preparation of nitrosamine free cinacalcet and salts thereof 发明人:BIRARI DILIP RAMDAS; SHINDE GORAKSHANATH BALASAHEB; TELDHUNE Ashish Pramod 权利人:MEGAFINE PHARMA P LTD; BIRARI DILIP RAMDAS; SHINDE GORAKSHANATH BALASAHEB; TELDHUNE Ashish Pramod 摘要:The present invention relates to a process for preparation of nitrosamine free Cinacalcet (1) and salts thereof. Wherein, Cinacalcet (1) and its salts is substantially free of nitrosamine impurities by using of an antioxidant in the process for synthesis of Cinacalcet (1) and its pharmaceutically acceptable salts.
专利号:US-2010267988-A1 优先权日:2006-06-08 标 题:Processes for preparing intermediate compounds useful for the preparation of cinacalcet 发明人:SZEKERES TIBOR; REPASI JOZSEF; SZABO ANDRAS; MANGION BERNARDINO 权利人:MEDICHEM SA 摘要:The invention relates, in general, to an improved process for preparing compounds (e.g., 3-(3-trifluoromethylphenyl)propanal (Compound III, below)), which are key intermediates for the synthesis of cinacalcet, its salts and/or solvates thereof, as well as the use of such compounds prepared by such process for the preparation of cinacalcet and/or its salts or solvates.
专利号:US-10865163-B2 优先权日:2017-12-20 标题:Carbon dioxide as a directing group for C—H functionalization reactions involving Lewis basic amines, alcohols, thiols, and phosphines for the synthesis of compounds 发明人:YOUNG MICHAEL C; KAPOOR MOHIT 权利人:UNIV TOLEDO 摘要:Methods of synthesizing compounds using CO 2 as a directing group for C—H functionalization, and compounds made thereby, are described.
专利号:EP-1990333-A1 优先权日:2007-05-11 标题 :Process for the preparation of cinacalcet hydrochloride 权利人:SANDOZ AG 摘要:The present invention relates to a process for the preparation of cinacalcet hydrochloride which is industrially feasible and commercially viable. The synthesis of cinacalcet hydrochloride is carried out by the condensation of 3-trifluromethylphenyl propionic acid with R-(+)-1-(lnaphthyl)ethylamine.
1: Komaba H, Hamano T, Fujii N, Moriwaki K, Wada A, Masakane I, Nitta K, Fukagawa M. Parathyroidectomy vs Cinacalcet Among Patients Undergoing Hemodialysis. J Clin Endocrinol Metab. 2022 Jun 16;107(7):2016-2025. doi: 10.1210/clinem/dgac142. 35(9):1679-1697. doi: 10.1007/s00467-020-04516-4. Epub 2020 May 4. 3: Block GA, Bushinsky DA, Cheng S, Cunningham J, Dehmel B, Drueke TB, Ketteler M, Kewalramani R, Martin KJ, Moe SM, Patel UD, Silver J, Sun Y, Wang H, Chertow GM. Effect of Etelcalcetide vs Cinacalcet on Serum Parathyroid Hormone in Patients Receiving Hemodialysis With Secondary Hyperparathyroidism: A Randomized Clinical Trial. JAMA. 2017 Jan 10;317(2):156-164. doi: 10.1001/jama.2016.19468. 23(3):485-501. doi: 10.1007/s11154-021-09694-6. Epub 2022 Jan 18. 6(6):587-92. 42:1-90. doi: 10.1016/bs.podrm.2017.02.001. Epub 2017 Apr 3. 28(6):594-603. doi: 10.1111/sdi.12413. Epub 2015 Aug 12. 13 Suppl
合成参考文献
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