CAS: 57-63-6; 17α-Ethynylestradiol

上下游产品

CAS号68-22-4 炔诺酮 | CAS号1111-63-3 Potassium acetylide | CAS号28913-23-7 17 alpha-ethiny... | CAS号53-16-7 雌酚酮 | CAS号74-86-2 乙炔 | CAS号4301-14-8 乙炔基溴化镁 | CAS号72-33-3 美雌醇 | CAS号60134-76-1 乙炔雌二醇3-β-D-葡糖醛酸 | CAS号75803-36-0 ethinyl estradi... | CAS号24560-70-1 Ethynylestradio... | CAS号75803-37-1 17-ethynyl-1,3,... | CAS号75803-39-3 乙炔雌二醇17-β-D-葡糖醛酸 | CAS号75812-41-8 17-ethynyl-1,2,... | CAS号38002-18-5 6-酮乙炔雌二醇 | CAS号50394-89-3 2-羟基炔雌醇 | CAS号50394-90-6 4-羟基乙炔基雌二醇 | CAS号50-28-2 雌二醇

炔诺酮置于cephalosporium Aphidicola (Imi 68689)体系中,用 二甲基亚砜 作为反应溶剂,化学反应 192.0H,以164 Mg的收率获得产物炔雌醇
参考文献:Microbial Transformation Of Antifertility Agents,Norethisterone And 17α-Ethynylestradiol
标题:Microbial Transformation Of Antifertility Agents,Norethisterone And 17α-Ethynylestradiol
摘要:口服避孕药瑞诺酮(1)经过头孢菌属蚜生青霉(cephalosporium Aphidicola)的微生物转化,反应生成了一个氧化代谢物,17α-乙炔基雌二醇(2),而2经过美洲线虫毛霉(cunninghamella Elegans)的微生物转化,产生了几种代谢物,包括19-去-17α-孕烷-1,3,5(10)-三烯-20-炔-3,4,17β-三醇(3),19-去-17α-孕烷-1,3,5(10)-三烯-20-炔-3,7α,17β-三醇(4),19-去-17α-孕烷-1,3,5(10)-三烯-20-炔-3,11α,17β-三醇(5),19-去-17α-孕烷-1,3,5(10)-三烯-20-炔-3,6β,17β-三醇(6)和19-去-17α-孕烷-1,3,5(10)-三烯-20-炔-3,17β-二醇-6β-甲氧基(7).代谢物7被发现是一种新化合物.这些代谢物是基于光谱技术进行结构鉴定的.
DOI:10.1515/znb-2004-0314

专利信息

专利号:EP-1641812-B1
优先权日:2003-06-30
标题 :PURE d-(17alpha)-13-ETHYL-17-HYDROXY-18,19-DINORPREGN-4-ENE-20-YNE-3-ONE-3E- AND -3Z-OXIME ISOMERS, AS WELL AS PROCESS FOR THE SYNTHESIS OF THE MIXTURE OF ISOMERS AND THE PURE ISOMERS
发明人：TUBA ZOLTAN; MAHO SANDOR; KESERU GYOERGY; KOZMA JOZSEF; HORVATH JANOS; BALOGH GABOR
权利人:RICHTER GEDEON NYRT
摘要:The invention relates to the pure d-(17alpha)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene-­20-yne-3-one-3E-oxime isomer of formula (IA), the pure d-(17alpha)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene-20-yne-3-one-3Z-oxime isomer of formula (IB), which are of gestagen activity, as well as the process for the synthesis of the mixture of the above isomers and the pure isomers. The invention also relates to the pharmaceutical compositions - and the process for their synthesis - which contain either the pure isomer of formula (IA) or the pure isomer of formula (IB) as active ingredient as such or in combination with other active ingredients (for example an oestrogen agent) together with pharmaceutical auxiliary materials commonly used in practice.

专利号:EP-1638988-B1
优先权日:2003-06-30
标题:Process for the synthesis of high purity d-(17alpha)-13-ethyl-17hydroxy-18,19-dinorpre:gn-4-ene-20-yne-3-one-oxime
发明人：TUBA ZOLTAN; MAHO SANDOR; KISS JANOS; MAGYARI ENDRENE; TERDY LASZLO
权利人:RICHTER GEDEON NYRT
摘要:The invention relates to a process for the synthesis of high purity d-(17alpha)-13-ethyl-17­hydroxy-18,19-dinorpregn-4-ene-20-yne-3-one-oxime (further on norelgestromine) via acetylation of d-norgestrel at position 17, oximation of the oxo group at position 3 of the obtained 17-acetoxy derivative, and finally hydrolyzing the acetoxy group at position 17 of the obtained 3-oxime derivative. The process according to our invention is as follows: the starting material, d-(17alpha-17-hydroxy-13-ethyl-18,19-dinorpregn-4-ene-20-yne-3­one (d-norgestrel) - purity 93-94 % - is acetylated with acetic anhydride in acetic acid, in the presence of zinc chloride and hydrogen chloride, or 70 % perchloric acid in an inert gas atmosphere, and after completion of the reaction the excess of acetic anhydride and the 'enol acetate' by-product are decomposed with aqueous hydrochioric acid, then the formed d-(17alpha)-17-acetoxy-13-ethyl-18,19-dinorpregn-4-ene-20-yne-3-one is isolated from the reaction mixture by addition of ice-water, the precipitated product is filtered off, washed with water, dried, dissolved in dichloromethane or acetone and clarified with silica gel or aluminum oxide and charcoal, after filtration of the clarifier the resulted solution is concentrated and the residue is recrystallized, the obtained d-(17alpha)-17-acetoxy-13-ethyl-18,19-dinorpregn-4-ene-20-yne-3-one is reacted either with hydroxylammonium acetate or with hydroxylammonium chloride in the presence of sodium acetate, in acetic acid in nitrogen atmosphere under vigorous stirring for about 1 hour, after completion of the reaction water is added, the precipitated product is filtered off, washed with water, dried and recrystallized, the obtained d-(17alpha-17-acetoxy-13-ethyl-18,19-dinorpregn-4-ene-20-yne-3-one-oxime is hydrolyzed with an equivalent amount of an alkali metal hydroxide in a C1-C4 alkanol solution, in nitrogen atmosphere between a temperature of about 5-38 °C, under vigorous stirring, after completion of the reaction the mixture is diluted with water and the pH of the resulted suspension is adjusted to 7,5-9 with acetic acid, the precipitated product is filtered off, washed with water, dried, the crude product is dissolved in ethanol, clarified with charcoal, and after filtration of the clarifier water is added to the obtained solution, the precipitated high purity d-(17alpha)-17-acetoxy-13-ethyl-18,19-dinorpregn-4-ene-20-yne-3-one-oxime is filtered off, washed with water and in given case recrystallized from ethanol.

专利号:US-12221452-B2
优先权日:2017-10-04
标题:Synthesis of cantharidin
发明人：DAVIDSON MATTHEW GENE; EKLOV BRIAN MATTHEW; WUTS PETER; LOERTSCHER BRAD MELVIN; SCHOW STEVEN R
权利人:VERRICA PHARMACEUTICALS INC
摘要:The invention provides synthetic methods for the preparation of cantharidin and analogs thereof. In one aspect, the invention provides an improved Diels-Alder cycloaddition to generate a key intermediate en route to cantharidin and analogs thereof. In certain embodiments, the new Diels-Alder reaction involves reacting Compound (2) in the presence of furan, and in the absence of acid or increased pressure, in an aprotic polar solvent with slight warming, to yield Compound (1) in favorable yield and exo-endo ratio. In another aspect, the invention also provides a new Diels-Alder reaction between compounds of Formula (III) and furan to yield compounds of Formula (IV), which can then be transformed into cantharidin or analogs thereof. In yet another aspect, the invention describes a new palladium-mediated carbonylation providing another key intermediate en route to cantharidin and analogs thereof. In addition to synthetic methods, present invention also provides compounds (i.e., intermediates) useful in the synthesis of cantharidin and analogs thereof. Compounds provided herein may have biological activity, and therefore may be used in the treatment of diseases or conditions (e.g., infectious diseases and skin conditions).

专利号:US-7816546-B2
优先权日:2003-06-30
标 题:Process for the synthesis of high purity d-(17α)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene-20-yn-3-one-oxime
发明人：TUBA ZOLTAN; MAHO SANDOR; KISS JANOS; MAGYARI ENDRENE; TERDY LASZLO
权利人:RICHTER GEDEON VEGYESZET
摘要:The invention relates to a process for the synthesis of d-(17α)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene-20-yn-3-one-oxime (also known as norelgestromin) via acetylation of d-norgestrel at position 17; oximation of the oxo group at position 3 of the obtained d-(17α)-13-ethyl-17-(acetyloxy)-18,19-dinorpregn-4-ene-20-yn-3-one; and then hydrolyzing the acetyloxy group at position 17 of the obtained d-(17α)-13-ethyl-17-(acetyloxy)-18,19-dinorpregn-4-ene-20-yn-3-oxime derivative, thereby obtaining norelgestromin.

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-7109377-B2
优先权日:1996-10-16
标 题:Synthesis of combinatorial libraries of compounds reminiscent of natural products
发明人：SCHREIBER STUART L; SHAIR MATTHEW D; TAN DEREK S; FOLEY MICHAEL A; STOCKWELL BRENT R
权利人:HARVARD COLLEGE
摘要:The present invention provides complex compounds reminiscent of natural products and libraries thereof, as well as methods for their production. The inventive compounds and libraries of compounds are reminiscent of natural products in that they contain one or more stereocenters, and a high density and diversity of functionality. In general, the inventive libraries are synthesized from diversifiable scaffold structures, which are synthesized from readily available or easily synthesizable template structures. In certain embodiments, the inventive compounds and libraries are generated from diversifiable scaffolds synthesized from a shikimic acid based epoxyol template. In other embodiments, the inventive compounds and libraries are generated from diversifiable scaffolds synthesized from the pyridine-based template isonicotinamide. The present invention also provides a novel ortho-nitrobenzyl photolinker and a method for its synthesis. Furthermore, the present invention provides methods and kits for determining one or more biological activities of members of the inventive libraries. Additionally, the present invention provides pharmaceutical compositions containing one or more library members.