CAS: 7759-35-5; Nestoron

该化合物是一种主要用于荷尔蒙避孕和荷尔蒙替代疗法的合成蛋白质,其特征是其高能和选择性,对孕酮受体具有有效抑制排卵和调节月经循环的作用,内斯托松酮以其有利的药理动因特征而著称,包括长半衰期和通过口服,转基因或肌肉内等各种途径进行控制的能力.其化学结构允许它模仿天然激素先质,导致类似的生物影响,同时尽量减少和诱导活动.这种选择性特别有利于减少通常与其他先质相关的副作用.内斯托松酮还在研究其在治疗内分泌硬化症和某些癌症等条件下的潜在应用.与任何激素制剂一样,由于潜在的副作用和反作用,应认真监测其使用.

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16-Methylene-17α-Hydroxy-17β-Acetyl-19-Norandrosta-4-En-3-One 06/08/7690

合成工艺路线路线简述

    反应生成 醋酸烯诺孕酮
    参考文献:Synthesewege Zum 17α‐hydroxy‐16‐methylen‐19‐nor‐progesteron Und Seinen Derivaten
    标题:Synthesewege Zum 17α‐hydroxy‐16‐methylen‐19‐nor‐progesteron Und Seinen Derivaten
    摘要:Abstractverschiedene Synthesewege Zum 17α‐hydroxy‐16‐methylen‐19‐nor‐progesteron (4A) Und Seinen Derivaten Werden Beschrieben. Die C‐19‐funktionalisierung Wird In Jedem Falle über Eine Barton‐reaktion Durchgeführt. Zum Teil Bisher Nicht Beschriebene Nebenprodukte Dieser Reaktion Und Der Folgereaktionen Werden Isoliert Und Aufgeklärt. Sie Gestatten Einen Genaueren Einblick In Die Reaktionsabläufe.
    DOI:10.1002/cber.19691020231

    海关参考信息

    专利信息


    专利号:WO-2004101594-A1
    优先权日:2003-05-14
    标题 :New mono-and bismethylene-steroid derivatives and process for their synthesis
    发明人:TUBA ZOLTAN; DANCSI LAJOSNE; FRANCSICSNE CZINEGE ERZSEBET; FALKAY GYOERGY; ZUPKO ISTVAN; MARKI ARPAD; MOLNAR CSABA; CSOERGEI JANOS; DUKATNE ABROK VILMA; BALOGH GABOR; MAK MARIANNA
    权利人:RICHTER GEDEON VEGYESZET; TUBA ZOLTAN; DANCSI LAJOSNE; FRANCSICSNE CZINEGE ERZSEBET; FALKAY GYOERGY; ZUPKO ISTVAN; MARKI ARPAD; MOLNAR CSABA; CSOERGEI JANOS; DUKATNE ABROK VILMA; BALOGH GABOR; MAK MARIANNA
    摘要:The invention relates to new mono- and bismethylene-steroid derivatives of general formula (I) - wherein Z represents two hydrogen atoms or an oxo group; X and Y independently of each other represent either two hydrogen atoms of a CH2= group, with the restriction that at least one of them is CH2= group and if the meaning of Z is oxo group Y represents two hydrogen atoms, R represents a C1-C4 alkyl group, as well as the pharmaceutical compositions containing the above compounds as active ingredients, and the processes for the synthesis of active ingredients and pharmaceutical compositions. The invention also relates to the methods of treatments with these compounds, which means administering to a mammal to be treated with progestogen - including human - effective amount/amounts of the active ingredients of the present invention as such or as medicament. The mono- and bismethylene-steroid derivatives of the general formula (I) have progestogen effect. They can be used as active ingredients of contraceptive medicaments as such or in combination with an estrogen component. Furthermore, they can be used in the treatment of endometriosis and in the substitution therapy of estrogen as gestagen agent beside the estrogen component. The mono- and bismethylene-steroid derivatives of the general formula (I) of the present invention can be synthesized by reacting a compound of the general formula (II), - wherein the meaning of Z, X and Y is as described for the compounds of formula (I) - with an acid anhydride of the general formula (R-CO)2O or with an acid chloride of the general formula R-CO-Cl - wherein R represents a C1-C4 alkyl group - in the presence of a strong acid.
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    主要参考文献


    1: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Segesterone Acetate. 2024 Aug 15. 101(10):618-620.
    73:101136. doi: 10.1016/j.yfrne.2024.101136. Epub 2024 Apr 25. 115(6):1369-1376. doi: 10.1016/j.fertnstert.2021.03.047. Epub 2021 Apr 27.
    5: Gemzell-Danielsson K, Sitruk-Ware R, Creinin MD, Thomas M, Barnhart KT, Creasy G, Sussman H, Alami M, Burke AE, Weisberg E, Fraser I, Miranda MJ, Gilliam M, Liu J, Carr BR, Plagianos M, Roberts K, Blithe D. Segesterone acetate/ethinyl estradiol 12-month contraceptive vaginal system safety evaluation. Contraception. 2019 Jun;99(6):323-328. doi: 10.1016/j.contraception.2019.02.001. Epub 2019 Mar 1.

    合成参考文献


    参考文献:10.1186/1471-2407-8-166
    摘要:Fu XD, Giretti MS, Goglia L, Flamini MI, Sanchez AM, Baldacci C, Garibaldi S, Sitruk-Ware R, Genazzani AR, Simoncini T. Comparative actions of progesterone, medroxyprogesterone acetate, drospirenone and nestorone on breast cancer cell migration and invasion. BMC Cancer. 2008 Jun 09;8():166.
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