Richter Gedeon Nyrt.

Richter Gedeon Vegyeszeti Gyar Rt

Marvishi Pharmaceutical Co., Ltd.

Sándor Mahó

Csaba Sánta

Gábor Balogh

Zoltan Tuba

János Csörgei

János Horváth

Zoltán Tuba

Antal Aranyi

Zoltán Béni

Janos Csorgei

Laszlo Szporny

Eva Palosi

Bela Kiss

Aniko Gere

Pal Vittay

József Bódi

László Terdy

Janos Szeles

Zoltan Beni

Janos Horvath

Judit Horvath

Csaba Szantay

Sandor Gorog

Ferenc Trischler

Gyorgy Visky

Maria Gazdag

György M Keserü

E Szilveszter Vizi

Peter Horvath

Maria Incze

Adam Demeter

Janos Brlik

Tamas Mester

Judit Horváth

Balazs Havasi

Csaba Molnar

Ferenc Soti

György Gálik

Béla Sörös

Lajosné Dancsi

György Visky

József Kozma

Csaba Molnár

Endréné Magyari

János Kiss

Ádám Demeter

Bela Soros

Gyorgy Galik

Jozsef Bodi

Gábor Szabó

Tamás Schäfer

László Balogh

Katalin Ferenczi

Krisztina Lancos

Arpad Trompler

Gabriella Szilagyi

Erika Bakcsi

Róbert Lovas

Anita Horváth

Ildikó Bacsa

Beatrix Mayer

János Széles

Erzsebet C Francsicsne

Anna M Boorne

Zsuzsa Baloghne Kardos

Francis F Foldes

Péter Vincze

Zoltán Horváth

Laszlo Terdy

Zoltan Horvath

Anita Horvath

Gábor SzabÓ

Balázs Havasi

The invention relates to the preparation of estetrol of formula (I), derivatives thereof protected at positions 3,15&#x3b1;,16&#x3b1;,17&#x3b2; of general formula (III), and 3-hydroxy derivatives thereof protected at positions 15&#x3b1;,16&#x3b1;,17&#x3b2; of general formula (IV), and to the intermediates of general formulae (III) and (IV) applied in the process. Another aspect of the invention is the use of estetrol of formula (I) obtained by the process of the invention for the preparation of a pharmaceutical composition. 

Industrial process for the preparation of high purity estetrol

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 process for the synthesis of compounds of formula (I), wherein the meaning of R is dimethylamino or acetyl group, using the compound of formula (III) or (IV), wherein the meaning of R' is dimethylamino or 2-methyl-1,3-dioxan-2-yl group, as starting material and methoxymethyl lithium as reagent. 

Process for the production of 21-methoxy-11-beta-phenyl-19-nor-pregna-4,9-diene-3,20-dione derivatives

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 present invention relates to novel crystalline Form A of 17&#x3b1;-acetoxy-21-methoxy-11&#x3b2;-[4-N,N-dimethylaminophenyl]-19-norpregna-4,9-diene-3,20-dione, (also known as CDB-4124) and methods for the preparation of it in excellent purity. 

Crystalline form of antiprogestin CDB-4124

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 relates to an industrial process for the preparation of 17-hydroxy-6&#x3b2;,7&#x3b2;;15&#x3b2;,16&#x3b2;-bismethylene-3-oxo-17&#x3b1;-pregn-4-ene-21-carboxylic acid &#x3b3;-lactone of formula (I), and to the key-intermediates for this process. 

Industrial process for the preparation of 17-hydroxy-6beta,7beta;15beta, 16beta-bismethylene-3-oxo-17alpha-pregn-4-ene-21-carboxylic acid y-lactone and key intermediates for this process

The present invention relates to a process for the synthesis of the 17-acetoxy-11&#x3b2;-[4-(dimethylamino)-phenyl]-21-methoxy-19-norpregna-4,9-dien-3,20-dione of formula (I): from 3,3-[1,2-etandiyl-bis(oxy)]-oestr-5(10),9(11)-dien-17-one of formula (II): 

Industrial method for the synthesis of 17-acetoxy-11&#x3b2;[4-(dimethylamino)-phenyl]-21-methoxy-19-norpregna-4,9-dien-3,20-dione and the key intermediates of the process

The invention relates to a process for the synthesis of d-(17&#x3b1;)-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-(17&#x3b1;)-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-(17&#x3b1;)-13-ethyl-17-(acetyloxy)-18,19-dinorpregn-4-ene-20-yn-3-oxime derivative, thereby obtaining norelgestromin.

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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

The invention relates to a new process for the synthesis of 17&bgr;-hydroxy-17&agr;-methyl-2-oxa-5&agr;-androstane-3-one of formula (I). The process according to the invention is as follows: the 17&bgr;-hydroxy-17&agr;-ethyl-1,3-seco-2-nor-5&agr;-androstane-1,3-diacid of formula (III) is transformed into the ring-closed 17&bgr;-hydroxy-17&agr;-methyl-1,3-seco-2-nor-5&agr;-androstane-1,3-diacid anhydride of formula (II) in an inert solvent or without solvent with a C -C alkan acid anhydride or a substituted carbodiimide of formula R &mdash;N&boxH;C&boxH;N&mdash;R &mdash; wherein R and R independently are C -C alkyl group, C -C alkyl group substituted by tertiary or quaternary amino group or 1-3 phenyl group, C -C cycloalkyl group, aryl group substituted by 1-3 methoxy, tertiary amino, nitro, C -C alkyl group or 1-3 halogen atom&mdash;and the obtained compound of formula (II) is reduced regioselectively by a complex alkali metal hydride in an inert solvent The new 17&bgr;-hydroxy-17&agr;-methyl-1,3-seco-2-nor-5&agr;-androstane-1,3-diacid anhydride of formula (II) is also the subject of the invention.

Process for the synthesis of 17&bgr;-hydroxy-17&agr;-methyl-2-oxa-5&agr;-androstane-3-one

Process for the synthesis of a-nor-seco compounds with sterane skeleton

There is disclosed novel, therapeutically active androstane derivatives having neuromuscular blocking effect, which are substituted by a quaternary ammonium group in 16-position; pharmaceutically composition containing them; process for producing them; and novel intermediates for the production.

Androstane derivatives substituted by a quaternary ammonium group in

Steroids with pregnane skeleton, pharmaceutical compositions containing

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Budapest, Hungary

Sándor Mahó