ES2479943T3 - Procedimiento de obtención de 17α-acetoxi-11β-(4-N,N-dimetilaminofenil)-19-norpregna-4,9-dien-3,20-diona - Google Patents
Procedimiento de obtención de 17α-acetoxi-11β-(4-N,N-dimetilaminofenil)-19-norpregna-4,9-dien-3,20-diona Download PDFInfo
- Publication number
- ES2479943T3 ES2479943T3 ES04703805.4T ES04703805T ES2479943T3 ES 2479943 T3 ES2479943 T3 ES 2479943T3 ES 04703805 T ES04703805 T ES 04703805T ES 2479943 T3 ES2479943 T3 ES 2479943T3
- Authority
- ES
- Spain
- Prior art keywords
- norpregna
- acetoxy
- dimethylaminophenyl
- dione
- dien
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 6
- 239000013078 crystal Substances 0.000 abstract 2
- 208000014311 Cushing syndrome Diseases 0.000 abstract 1
- 208000010412 Glaucoma Diseases 0.000 abstract 1
- 230000001911 anti-progestational effect Effects 0.000 abstract 1
- 239000003433 contraceptive agent Substances 0.000 abstract 1
- 230000002254 contraceptive effect Effects 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 238000004090 dissolution Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000003862 glucocorticoid Substances 0.000 abstract 1
- 201000009395 primary hyperaldosteronism Diseases 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- -1 1,2-ethanedioxy Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- DOJXGHGHTWFZHK-UHFFFAOYSA-N Hexachloroacetone Chemical compound ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl DOJXGHGHTWFZHK-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000004973 alkali metal peroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 229940061607 dibasic sodium phosphate Drugs 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical group [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical group FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0077—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom
- C07J41/0083—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 substituted in position 11-beta by a carbon atom, further substituted by a group comprising at least one further carbon atom substituted in position 11-beta by an optionally substituted phenyl group not further condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
El procedimiento comprende (a) la formación de cristales del isopropanol hemisolvato de 17a-acetoxi-11ß-(4-N,N-dimetilaminofenil)-19-norpregna-4,9-dien-3,20-diona (VA-2914) por disolución en isopropanol y posterior cristalización; (b) la separación de los cristales de isopropanol hemisolvato de VA-2914. El compuesto VA-2914 es un esteroide con actividad anti-progestacional y anti-glucocorticoidal, útil en indicaciones ginecologías terapéuticas y anticonceptivas y en el tratamiento del síndrome de Cushing y del glaucoma.
Description
es útil para la síntesis de VA-2914. El carbinol acetato puede obtenerse mediante un procedimiento como el mostrado en el siguiente Esquema de Reacción. imagen6 O imagen7 O OAc
OAc
O
Me2N O
OAc
O
O OH
5
Brevemente, la obtención de carbinol acetato comprende, en una primera etapa, epoxidar el doble enlace 5(10) presente en la 17α-acetoxi-3,3-(1,2-etanodioxi)-19-norpregna-5,(10),9(11)-dien-20-ona mediante reacción de dicho compuesto con un aducto formado por la reacción de una cetona halogenada y un peróxido, en presencia de una base y de un disolvente. Dicha cetona halogenada puede ser una acetona halogenada, por ejemplo, 10 hexafluoracetona o hexacloroacetona. Cualquier peróxido apropiado puede ser utilizado en esta reacción, por ejemplo, peróxido de hidrógeno, un peróxido de un metal alcalino, un peroxiácido, etc. Esta reacción de epoxidación se lleva a cabo en presencia de una base, preferentemente, una base inorgánica, tal como, por ejemplo, un fosfato, carbonato o bicarbonato de un metal alcalino y de un disolvente orgánico, preferentemente, un disolvente halogenado. En una realización particular, la cetona halogenada es hexafluoroacetona, el peróxido es peróxido de
15 hidrógeno, la base es fosfato sódico dibásico y el disolvente es diclorometano.
A continuación, el epóxido obtenido se hace reaccionar, en una segunda etapa, con un reactivo de Grignard, tal como bromuro de 4-N,N-dimetilaminofenilmagnesio en presencia de una sal de Cu(I) para obtener el carbinol acetato.
Los siguientes Ejemplos ilustran la invención y no deben ser considerados como limitativos de la misma.
20 Ejemplo 1
Obtención de 17α-acetoxi-11β-(4-N,N-dimetilaminofenil)-19-norpregna-4,9-dien-3,20-diona [VA-2914] cruda
Se cargaron 38,5 g de 3,3-(1,2-etanodioxi)-5α-hidroxi-11β-(4-N,N-dimetilaminofenil)-17α-acetoxi-19-norpregna-9-en20-ona [carbinol acetato] purificado, en un matraz en atmósfera de nitrógeno, a una temperatura comprendida entre 20 ºC y 22 ºC y se añadieron 385 ml de agua desionizada y 17,91 g de HKSO4. La suspensión obtenida se agitó
25 hasta solución total, durante 4 h aproximadamente. El final de la reacción se determinó mediante cromatografía en capa fina (TLC).
6
Claims (1)
-
imagen1
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES200300162 | 2003-01-22 | ||
ES200300162A ES2212912B1 (es) | 2003-01-22 | 2003-01-22 | Procedimiento para la obtencion de 17alfa-acetoxi-11beta-(4-n,n-dimetilaminofenil)-19-norpregna-4,9-dien-3,20-diona. |
PCT/ES2004/000026 WO2004065405A1 (es) | 2003-01-22 | 2004-01-21 | PROCEDIMIENTO PARA LA OBTENCÍON DE 17α-ACETOXI-11β-(4-N,N-DIMETILAMINOFENIL)-19-NORPREGNA-4,9-DIEN-3,20-DIONA |
Publications (1)
Publication Number | Publication Date |
---|---|
ES2479943T3 true ES2479943T3 (es) | 2014-07-25 |
Family
ID=32749097
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES200300162A Expired - Fee Related ES2212912B1 (es) | 2003-01-22 | 2003-01-22 | Procedimiento para la obtencion de 17alfa-acetoxi-11beta-(4-n,n-dimetilaminofenil)-19-norpregna-4,9-dien-3,20-diona. |
ES04703805.4T Expired - Lifetime ES2479943T3 (es) | 2003-01-22 | 2004-01-21 | Procedimiento de obtención de 17α-acetoxi-11β-(4-N,N-dimetilaminofenil)-19-norpregna-4,9-dien-3,20-diona |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES200300162A Expired - Fee Related ES2212912B1 (es) | 2003-01-22 | 2003-01-22 | Procedimiento para la obtencion de 17alfa-acetoxi-11beta-(4-n,n-dimetilaminofenil)-19-norpregna-4,9-dien-3,20-diona. |
Country Status (11)
Country | Link |
---|---|
EP (2) | EP2348033A3 (es) |
JP (1) | JP2006515869A (es) |
KR (1) | KR20050107400A (es) |
CN (1) | CN100354300C (es) |
CA (1) | CA2514169C (es) |
CY (1) | CY1115343T1 (es) |
DK (1) | DK1602662T3 (es) |
ES (2) | ES2212912B1 (es) |
PT (1) | PT1602662E (es) |
SI (1) | SI1602662T1 (es) |
WO (1) | WO2004065405A1 (es) |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HU230492B1 (hu) | 1996-05-01 | 2016-08-29 | The Government Of The United States Of America | Új progesztációt gátló szerként használható 21-helyzetben szubsztituált progeszteron-származékok, ezeket tartalmazó gyógyszerkészítmények, alkalmazásuk |
US6900193B1 (en) | 1996-05-01 | 2005-05-31 | The United States Of America As Represented By The Department Of Health And Human Services | Structural modification of 19-norprogesterone I: 17-α-substituted-11-β-substituted-4-aryl and 21-substituted 19-norpregnadienedione as new antiprogestational agents |
CA2516319C (en) * | 2003-02-28 | 2012-09-18 | The Government Of The United States Of America, As Represented By The Se Cretary, Department Of Health And Human Services | Method for preparing 17.alpha.-acetoxy-11.beta.-(4-n,n-dimethylaminophenyl)-19-norpregna-4,9-diene-3,20-dione, intermediates thereof, and methods for the preparation of such intermediates |
CN100469786C (zh) * | 2005-06-20 | 2009-03-18 | 中国科学院理化技术研究所 | 合成16-脱氢孕甾双烯酮醇醋酸酯或同类物的方法 |
US20100261693A1 (en) | 2007-10-17 | 2010-10-14 | Ulmann Andre | Method for treating cushing's syndrome |
US8299050B2 (en) | 2008-01-29 | 2012-10-30 | Laboratoire Hra-Pharma | Method for treating uterine fibroids |
US8512745B2 (en) | 2008-12-08 | 2013-08-20 | Laboratoire Hra Pharma | Ulipristal acetate tablets |
PL2419108T3 (pl) | 2009-04-14 | 2017-08-31 | Laboratoire Hra Pharma | Sposób antykoncepcji na żądanie |
US8426392B2 (en) | 2009-12-09 | 2013-04-23 | Laboratoire Hra-Pharma | Method for providing emergency contraception |
US8962603B2 (en) | 2010-02-01 | 2015-02-24 | Laboratoire Hra-Pharma | Method for post coital contraception in overweight or obese female subjects using ulipristal acetate |
US20130045959A1 (en) | 2010-02-01 | 2013-02-21 | Andre Ulmann | Method for late post coital contraception using ulipristal acetate |
CN102241722B (zh) * | 2010-05-12 | 2015-11-25 | 杭州容立医药科技有限公司 | 一种合成孕酮受体调节剂优力司特的纯化方法 |
EP2471537A1 (en) | 2010-12-30 | 2012-07-04 | PregLem S.A. | Treatment of pain associated with dislocation of basal endometrium |
EP2545922A1 (en) | 2011-07-12 | 2013-01-16 | PregLem S.A. | Treatment of excessive menstrual bleeding associated with uterine fibroids |
CN102344478B (zh) * | 2011-07-22 | 2013-08-07 | 上海希迈医药科技有限公司 | 一种17α-乙酰氧基-11β-(4-N,N-二甲氨基苯基)-19-去甲孕甾-4,9-二烯-3,20-二酮的结晶物及其制备方法 |
CN102321141B (zh) | 2011-07-22 | 2013-05-15 | 上海希迈医药科技有限公司 | 一种17α-乙酰氧基-11β-(4-N,N-二甲氨基苯基)-19-去甲孕甾-4,9-二烯-3,20-二酮的无定形物及其制备方法 |
CN103193850A (zh) * | 2012-01-04 | 2013-07-10 | 北京紫竹药业有限公司 | 甾体化合物的新晶型及其制备方法 |
FR2987271B1 (fr) | 2012-02-28 | 2017-08-18 | Hra Pharma Lab | Combinaison de modulateurs selectifs du recepteur a la progesterone et d'anti-inflammatoires non steroidiens |
EP2641602A1 (en) | 2012-03-23 | 2013-09-25 | PregLem S.A. | Method for treating gynecological diseases |
CN103755765B (zh) * | 2012-04-17 | 2018-01-02 | 常州市第四制药厂有限公司 | 醋酸乌利司他的多晶型及其制备方法 |
HUE037889T2 (hu) | 2012-05-25 | 2018-09-28 | Hra Pharma Lab | Ulipristal acetát melltumorok megelõzésére és kezelésére |
CN102887931B (zh) * | 2012-07-07 | 2015-04-15 | 山东诚创医药技术开发有限公司 | 一种醋酸乌利司他的结晶体及其制备方法 |
ES2672509T3 (es) * | 2012-09-28 | 2018-06-14 | Aska Pharmaceutical Co., Ltd. | Forma polimórfica cristalina de acetato de ulipristal |
WO2014050105A1 (en) | 2012-09-28 | 2014-04-03 | Aska Pharmaceutical Co., Ltd. | Amorphous ulipristal acetate |
CA2885798A1 (en) | 2012-09-28 | 2014-04-03 | Aska Pharmaceutical Co., Ltd. | Crystalline polymorphic form of ulipristal acetate |
FR2997628B1 (fr) * | 2012-11-08 | 2015-01-16 | Hra Pharma Lab | Produit de co-micronisation comprenant un modulateur selectif des recepteurs a la progesterone |
FR2997627B1 (fr) * | 2012-11-08 | 2015-01-16 | Hra Pharma Lab | Produit de co-micronisation comprenant de l'ulipristal acetate |
FR2999081B1 (fr) | 2012-12-06 | 2015-02-27 | Hra Pharma Lab | Dispersion solide d'un modulateur selectif du recepteur a la progesterone |
WO2014167510A2 (en) | 2013-04-10 | 2014-10-16 | Preglem Sa | Progesteron receptor modulators for use in the therapy of uterine fibroids |
CN104418930B (zh) * | 2013-08-23 | 2018-01-12 | 四川海思科制药有限公司 | 一种高纯度醋酸乌利司他 |
FR3060389B1 (fr) | 2016-12-20 | 2019-05-31 | Laboratoire Hra-Pharma | Comprime enrobe comprenant de l'ulipristal acetate ou un de ses metabolites |
CN110028543B (zh) * | 2018-01-11 | 2024-04-12 | 上海汇伦医药股份有限公司 | 一种醋酸优力司特的制备方法 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4954490A (en) * | 1988-06-23 | 1990-09-04 | Research Triangle Institute | 11 β-substituted progesterone analogs |
US5929262A (en) | 1995-03-30 | 1999-07-27 | The United States Of America As Represented By The Department Of Health And Human Services | Method for preparing 17α-acetoxy-11β-(4-N, N-dimethylaminophyl)-19-Norpregna-4,9-diene-3, 20-dione, intermediates useful in the method, and methods for the preparation of such intermediates |
DE19747914A1 (de) * | 1997-10-30 | 1999-05-06 | Stihl Maschf Andreas | Abgasschalldämpfer |
US6020328A (en) * | 1998-03-06 | 2000-02-01 | Research Triangle Institute | 20-keto-11β-arylsteroids and their derivatives having agonist or antagonist hormonal properties |
AU775831B2 (en) * | 1999-12-29 | 2004-08-19 | Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services, The | Process for preparing 17alpha-acetoxy-11beta-(4-N,N-(dimethylamino)phenyl)-21- methoxy-19-norpregna-4,9-diene-3,20-dione, intermediates useful in the process, and processes for preparing such intermediates |
DK1265911T3 (da) * | 2000-03-17 | 2008-09-29 | Us Gov Health & Human Serv | 17-alfa-substitueret-11-beta-substitueret-4-aryl og 21-substitueret 19-norpregnadiendion som antiprogestationelle midler |
CA2516319C (en) * | 2003-02-28 | 2012-09-18 | The Government Of The United States Of America, As Represented By The Se Cretary, Department Of Health And Human Services | Method for preparing 17.alpha.-acetoxy-11.beta.-(4-n,n-dimethylaminophenyl)-19-norpregna-4,9-diene-3,20-dione, intermediates thereof, and methods for the preparation of such intermediates |
-
2003
- 2003-01-22 ES ES200300162A patent/ES2212912B1/es not_active Expired - Fee Related
-
2004
- 2004-01-21 SI SI200432173T patent/SI1602662T1/sl unknown
- 2004-01-21 EP EP10165052.1A patent/EP2348033A3/en not_active Withdrawn
- 2004-01-21 CA CA2514169A patent/CA2514169C/en not_active Expired - Lifetime
- 2004-01-21 ES ES04703805.4T patent/ES2479943T3/es not_active Expired - Lifetime
- 2004-01-21 PT PT47038054T patent/PT1602662E/pt unknown
- 2004-01-21 WO PCT/ES2004/000026 patent/WO2004065405A1/es active Search and Examination
- 2004-01-21 CN CNB2004800042263A patent/CN100354300C/zh not_active Expired - Lifetime
- 2004-01-21 KR KR1020057013651A patent/KR20050107400A/ko not_active Application Discontinuation
- 2004-01-21 EP EP04703805.4A patent/EP1602662B1/en not_active Expired - Lifetime
- 2004-01-21 JP JP2006500145A patent/JP2006515869A/ja active Pending
- 2004-01-21 DK DK04703805.4T patent/DK1602662T3/da active
-
2014
- 2014-07-18 CY CY20141100543T patent/CY1115343T1/el unknown
Also Published As
Publication number | Publication date |
---|---|
ES2212912A1 (es) | 2004-08-01 |
CY1115343T1 (el) | 2017-01-04 |
PT1602662E (pt) | 2014-06-25 |
DK1602662T3 (da) | 2014-07-07 |
EP2348033A2 (en) | 2011-07-27 |
EP1602662A1 (en) | 2005-12-07 |
CA2514169A1 (en) | 2004-08-05 |
CN100354300C (zh) | 2007-12-12 |
SI1602662T1 (sl) | 2014-08-29 |
ES2212912B1 (es) | 2005-10-01 |
KR20050107400A (ko) | 2005-11-11 |
CN1753905A (zh) | 2006-03-29 |
WO2004065405A1 (es) | 2004-08-05 |
EP1602662B1 (en) | 2014-04-23 |
EP2348033A3 (en) | 2013-05-22 |
JP2006515869A (ja) | 2006-06-08 |
CA2514169C (en) | 2013-10-08 |
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