CAS: 65928-65-6; 17α-Cyanomethyl-13β-Methyl-17β-Hydroxy-Gon-5(10)-En-3-On

📜3,3-Dimethoxy-17α-Cyanomethyl-17β-Hydroxy-5(10)-Estren 反应生成 地诺孕素ep杂质i
参考文献:Ponsold,K.;Menzenbach,B.;Huebner,M.;Oettel,M.;Barnikol-Oettler,K.;Te+
标题:Ponsold,K.;Menzenbach,B.;Huebner,M.;Oettel,M.;Barnikol-Oettler,K.;Te+

专利信息

专利号:EP-2256128-B1
优先权日:2009-05-22
标题 :Method for synthesis of dienogest from estrone-3-methylether
发明人：DOEHLER THOMAS; WERNER MICHAEL; WALTHER DIRK-DETLEF
权利人:HEYL CHEM PHARM
摘要:The invention concerns a method for the synthesis of dienogest from 3-methoxy-estra-1,3,5-trien-17-one is comprising the steps of a) reacting 3-methoxy-estra-1,3,5-trien-17-one with alcohol in the presence of an acid in an organic solvent to form 3-methoxy-17,17-dialkoxy-estra-1,3,5-triene; b) subjecting the product of step a) to partial reduction by reaction with alkali metal in liquid ammonia; c) treating the product of step b) with mild acid; d) reacting the product of step c) with cyanomethyl lithium; e) treating the product of step d) with oxalic acid and f) treating the product of step e) with pyridinium tribromide in pyridine to yield dienogest.

专利号:US-8314145-B2
优先权日:2005-12-05
标题 :High purity 17α-cyanomethyl-17β-hydroxy-estra-4,9-diene-3-one and process for the synthesis thereof
发明人：DANCSI LAJOSNE; MAHO SANDOR; ARANYI ANTAL; HORVATH JANOS
权利人:DANCSI LAJOSNE; MAHO SANDOR; ARANYI ANTAL; HORVATH JANOS; RICHTER GEDEON VEGYESZET
摘要:The invention relates to a new process for the synthesis of high purity 17α-cyanomethyl-17β-hydroxy-estra-4,9-diene-3-one (further on dienogest) of formula (I) from 3-methoxy-17-hydroxy-estra-2,5(10)-diene of formula (V). The invention relates also to the high purity 17α-cyanomethyl-17β-hydroxy-estra-4,9-diene-3-one and pharmaceutical compositions containing that as active ingredient. The pharmaceutical compositions according to this invention contain high purity dienogest of formula (I) in which the total amount of impurities is less than 0.1%, while the amount of 4-bromo-dienogest is under the detection limit (0.02%) as active ingredient or at least one of the active ingredients and auxiliary materials, which are commonly used in practice, such as carriers, excipients or diluents. According to our invention the dienogest of formula (I) is synthesized the following way: i) 3-methoxy-17-hydroxy-estra-2,5(10)-diene of formula (V) is reacted with aluminum isopropylate in the presence of cyclohexanone in an inert organic solvent under heating; ii) the so obtained 3-methoxy-estra-2,5(10)-diene-17-one of formula (IV) is reacted with cyanomethyl lithium at a temperature between 0 and −30° C.; iii) the obtained 3-methoxy-17α-cyanomethyl-17β-hydroxy-estra-2,5(10)-diene of formula (III) is reacted with a strong organic acid in tetrahydrofuran solution; iv) the obtained 17α-cyanomethyl-17β-hydroxy-estr-5(10)-ene-3-one of formula (II) is reacted with 1-1.5 equivalent of pyridinium tribromide in pyridine solution at a temperature between 0 and 60° C., then the obtained crude dienogest of formula (I) is purified by recrystallization and preparative HPLC.

专利号:US-5438134-A
优先权日:1990-07-09
标 题:Process for the production of unsaturated 17 α-cyanomethyl-17 β-h
发明人：TEICHMUELLER GERHARD; MUELLER GERD
权利人:JENAPHARM GMBH
摘要:The unsaturated 17α-cyanomethyl-17β-hydroxy steroids of the formula I, ##STR1## in which R 1 =Me, Eth; R 2 =H, Me; R 3 =H, OH, an acetoxy or alkoxy group; R 4 =H, R 5 =OH, an acetoxy, alkoxy group of R 4 and R 5 together represent a keto- or ketal group and double bonds are contained in the basic structure of the steroid, particularly between the 15 and 16 position in the steroid ring, from unsaturated 17-ketosteroids of the general formula II as described herein with the aforementioned meanings of R 1 to R 5 by reacting the unsaturated 17-ketosteroids with LiCH 2 CN and subsequently hydrolyzing. n The compounds of formula I are pharmacologically interesting steroid compounds or also intermediate products for the synthesis of highly-effective steroid products which can be used in human and veterinary medicine for the treatment of endocrine disorders and for reproductive control based on their specific hormonal/anti-hormonal actions. n The compounds are suitable for the treatment of endometriosis and also in combination with preparations with ethinylestradiol for fertility control.

专利号:US-2010298585-A1
优先权日:2009-05-22
标题 :Method for synthesis of dienogest from estrone-3-methylether

专利号:EP-2256128-A1
优先权日:2009-05-22
标题:Method for synthesis of dienogest from estrone-3-methylether