CAS: 159634-47-6; (R)-2-Amino-N-(3-(Benzyloxy)-1-(1-(Methylsulfonyl)Spiro[indoline-3,4'-Piperidin]-1'-yl)-1-Oxopropan-2-yl)-2-Methylpropanamide

该化合物是grelin受体的非植物激动剂,作为生长激素秘方,模仿grelin的行为,刺激生长激素(GH)和胰岛素类似生长因子1(IGF-1)的释放,但不影响皮质素或蛋白素水平,它的口服生物利用率和长期半衰期使它成为研究肌肉生长,骨密度和代谢调节的研究环境的感兴趣对象.与基于Peptid的密座不同,Ibutamoren不需要注射,为实验应用提供了实际优势.其行动机制为调查与GH有关的老化,石球和代谢紊乱症路径提供了工具.

结构式图片

欧盟法规

C&L通报

上下游产品

CAS号159634-87-4 TC6N | CAS号498-94-2 4-哌啶甲酸 | CAS号10314-98-4 N-Cbz-哌啶-4-羧酸 | CAS号138163-08-3 4-甲酰基-N-Cbz-哌啶 | CAS号10314-99-5 N-Cbz-哌啶-4-甲酰氯 | CAS号100-63-0 苯肼 | CAS号184289-85-8 benzyl spiro[in... | CAS号167484-18-6 螺[吲哚啉-3,4'-哌啶]-... | CAS号47173-80-8 N-B°C-O-苄基-D-丝氨酸

合成工艺路线路线简述

  • 合成目标产物 Mk-677 主要起始原料 1-[(Benzyloxy)Carbonyl]Piperidine-4-Carboxylic Acid
  • (文献来源)合成步骤主要原料 1-[(Benzyloxy)Carbonyl]Piperidine-4-Carboxylic Acid
螺[吲哚啉-3,4'-哌啶]-1'-羧酸苄酯置于palladium On Activated Charcoal 甲烷磺酸,氢气,1-羟基苯并三唑,N,N-二异丙基乙胺,N,N'-二环己基碳二亚胺体系中,用 四氢呋喃,乙醇,水 用作溶剂,5.0~65.0 °C,275.79 Kpa 条件下,反应 21.5H,反应生成伊布莫仑
参考文献:合成基于口服螺螺吲哚的生长激素促分泌素mk-677
标题:合成基于口服螺螺吲哚的生长激素促分泌素mk-677
摘要:默克生长激素促分泌素的制备;描述了mk-677.费歇尔吲哚/还原为基础的策略提供了这种有效化合物的新型螺二氢吲哚核.该优化的序列仅需要分离一种中间体10并从异二十二烯酸3提供48%的总收率的mk-677 .
Doi:10.1016/s0040-4020(97)00359-1

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-2015158809-A9
优先权日:2013-02-26
标 题 :Method of making 1-(acyloxy)-alkyl carbamate compounds
发明人:WANG HUAN; LIU PENG; DAI QUNYING; YIN HAO; RAILLARD STEPHEN P
权利人:XENOPORT INC
摘要:Methods of preparing carbamate prodrugs of amine-containing drugs are provided. Carbonates useful in the synthesis of the carbamate prodrugs are also provided.

专利号:CA-2551859-C
优先权日:2003-12-30
标题 :Synthesis of acyloxyalkyl carbamate prodrugs and intermediates thereof

专利号:EP-2250143-A2
优先权日:2008-01-25
标题 :Method for the enzymatic kinetic resolution of acyloxyalkyl thiocarbonates used for the synthesis of acyloxyalkyl carbamates

专利号:WO-2005066122-A2
优先权日:2003-12-30
标题 :Synthesis of acyloxyalkyl carbamate prodrugs and intermediates thereof

专利号:EP-2250143-B1
优先权日:2008-01-25
标 题 :Method for the enzymatic kinetic resolution of acyloxyalkyl thiocarbonates used for the synthesis of acyloxyalkyl carbamates
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✅ COA系统入驻 | 共享模式

主要参考文献


1: Van Wagoner RM, Eichner A, Bhasin S, Deuster PA, Eichner D. Chemical Composition and Labeling of Substances Marketed as Selective Androgen Receptor Modulators and Sold via the Internet. JAMA. 2017 Nov 28;318(20):2004-2010. doi: 10.1001/jama.2017.17069. Erratum in: JAMA. 2018 Feb 20;319(7):724.
2: Sigalos JT, Pastuszak AW. The Safety and Efficacy of Growth Hormone Secretagogues. Sex Med Rev. 2018 Jan;6(1):45-53. doi: 10.1016/j.sxmr.2017.02.004. Epub 2017 Apr 8. Review.
3: Harmatz ES, Stone L, Lim SH, Lee G, McGrath A, Gisabella B, Peng X, Kosoy E, Yao J, Liu E, Machado NJ, Weiner VS, Slocum W, Cunha RA, Goosens KA. Central Ghrelin Resistance Permits the Overconsolidation of Fear Memory. Biol Psychiatry. 2017 Jun 15;81(12):1003-1013. doi: 10.1016/j.biopsych.2016.11.009. Epub 2016 Nov 29.

合成参考文献


参考文献:10.1385/endo:16:3:195
摘要:Malmlöf K, Bauer MK, Johansen PB, Ankersen M, Veldhuis JD. Daily low-dose administration of growth hormone secretagogue stimulates pulsatile growth hormone secretion and elevates plasma insulin-like growth factor-1 levels in pigs. Endocrine. 2001 Dec;16(3):195–9. doi: 10.1385/endo:16:3:195.
参考文献:10.1007/bf03041053
摘要:Schmidt A, Fabrizii V, Maier C, Riedl M, Schmidt A, Kotzmann H, Geyer G, Luger A. Normal regulation of elevated plasma ghrelin concentrations in dialysis patients. Wien Klin Wochenschr. 2004 Apr 30;116(7-8):235–9. doi: 10.1007/bf03041053.
参考文献:10.1007/s13539-014-0149-7
摘要:Morley JE, von Haehling S, Anker SD. Are we closer to having drugs to treat muscle wasting disease J cachexia sarcopenia muscle. 2014 May 28;5(2):83–7. doi: 10.1007/s13539-014-0149-7.
参考文献:10.2165/00126839-199901030-00001
摘要:Reginster JY, Henrotin Y, Gosset C. Promising new agents in osteoporosis. Drugs R D. 1999 Mar;1(3):195–201. doi: 10.2165/00126839-199901030-00001.
参考文献:10.2165/00126839-199901030-00002
摘要:Peters DC, Coleman SG. Osteoporosis. Summary and table. Drugs R D. 1999 Mar;1(3):203–9. doi: 10.2165/00126839-199901030-00002.
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