Richter Gedeon Nyrt.

Richter Gedeon Vegyeszeti Gyar Rt

Vasipari Kutato Es Fejleszto Vallalat

Nehezipari Muszaki Egyetem

János Horváth

Sándor Mahó

János Csörgei

Csaba Sánta

Zoltán Béni

Antal Aranyi

Gábor Balogh

Zoltán Tuba

György M Keserü

József Kozma

Lajosné Dancsi

Sandor Nagy

Andras Pethes

Akos Ban

Péter Vincze

Jozsef Meszaros

Anita Horváth

Janos Sziklavari

Imre Bader

Endre Berecz

László Balogh

Gabor Szina

Lajos Schottner

The invention relates to the last step of a synthetic process, in which Nomegestrol-acetate of formula (I) is synthesized from 17&#x3b1;-acetoxy-6-methylene-19-norpregn-4-ene-3,20-dione of formula (II) in the presence of Pd/C catalyst and acetic acid in hot ethanolic solution. 

Industrial process for the synthesis of nomegestrol-acetate

The present invention relates to a new process for the synthesis of compounds of formula (I) (wherein the meaning of R is dimethylamino or acetyl group) using the compound of formula (II) (wherein the meaning of R is dimethylamino or 2-methyl-1,3-dioxolan-2-yl group) as starting material, as well as to the intermediate of the process. 

Industrial process for the synthesis of ulipristal acetate and its 4'-acetyl analogue

The present invention relates to a new stereoselective process for the synthesis of 17(&#x3b1;)-17-acetyl-17-hydroxy-estr-4-en-3-one of formula (I), as well as to the new intermediates of the process. The 17(&#x3b1;)-17-acetyl-17-hydroxy-estr-4-en-3-one (gestonorone) is an important intermediate in the synthesis of the active ingredients having progestogen activity&#x2014;such as gestonorone capronate and nomegestroi acetate. Formulas (I), (II) and (III). 

Process for the production of 19-norpregn-4-en-3,20-dione-17&#x3b1;-ol(gestonorone) and intermediates therefor

The invention relates to a new process for the synthesis of high purity 17&#x3b1;-cyanomethyl-17&#x3b2;-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 17&#x3b1;-cyanomethyl-17&#x3b2;-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 &#x2212;30&#xb0; C.; iii) the obtained 3-methoxy-17&#x3b1;-cyanomethyl-17&#x3b2;-hydroxy-estra-2,5(10)-diene of formula (III) is reacted with a strong organic acid in tetrahydrofuran solution; iv) the obtained 17&#x3b1;-cyanomethyl-17&#x3b2;-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&#xb0; C., then the obtained crude dienogest of formula (I) is purified by recrystallization and preparative HPLC. 

High purity 17&#x3b1;-cyanomethyl-17&#x3b2;-hydroxy-estra-4,9-diene-3-one and process for the synthesis thereof

The invention is directed to a process of preparing substantially pure d-(17&#x3b1;)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene-20-yn-3-one-3E- and -3Z-oxime isomers, as well as a process for the synthesis of the mixture of isomers and the pure isomers. The invention also relates to substantially pure d-(17&#x3b1;)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene20-yn-3-one-3E-oxime and substantially pure d-(17&#x3b1;)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene-20-yn-3-one-3Z-oxime isomer. Further aspects of the invention include a composition comprising substantially pure d-(17&#x3b1;)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene20-yn-3-one-3E-oxime or substantially pure d-(17&#x3b1;)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-ene-20-yn-3-one-3Z-oxime isomer, and methods of treatment using said compositions.

Process of making isomers of norelgestromin and methods using the same

An analytical apparatus for determining the cryolite concentration in a cryolite-alumina electrolysis cell. The apparatus uses a reference electrode comprising a solid oxygen electrolyte tube containing a reference electrode of a cryolite melt supersaturated with alumina. A measuring electrode is combined with such a reference electrode to provide a potential representative of alumina concentration in the alumina electrolysis cell.

Apparatus for determination of aluminum oxide content of the cryolite

The invention relates to a process for the removal of contaminating chemical elements from pig-iron, steel and other metals and metal alloys in course of the refining process with oxygen blast, as well as for accelerating hydrometallurgical processes. The essence of the process lies in that quantity of free oxygen radicals and temperature of smelting bath are controlled.

Process for the removal of contaminating elements from pig-iron, steel,

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Budapest, Hungary

János Horváth