MXPA05013948A - Proceso para la sintesis de d-(17a)-13-etil-17-hidroxi-18 19-dinor-pregn-4-ene-20-ina-3-ona-oxima. - Google Patents
Proceso para la sintesis de d-(17a)-13-etil-17-hidroxi-18 19-dinor-pregn-4-ene-20-ina-3-ona-oxima.Info
- Publication number
- MXPA05013948A MXPA05013948A MXPA05013948A MXPA05013948A MXPA05013948A MX PA05013948 A MXPA05013948 A MX PA05013948A MX PA05013948 A MXPA05013948 A MX PA05013948A MX PA05013948 A MXPA05013948 A MX PA05013948A MX PA05013948 A MXPA05013948 A MX PA05013948A
- Authority
- MX
- Mexico
- Prior art keywords
- oxime
- 17alpha
- yne
- ene
- hydroxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 229960004400 levonorgestrel Drugs 0.000 abstract 1
- 238000006146 oximation reaction Methods 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 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
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
- C07J41/0016—Oximes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0081—Substituted in position 17 alfa and 17 beta
- C07J1/0088—Substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0096—Alkynyl derivatives
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)
- Saccharide Compounds (AREA)
Abstract
La invencion se refiere a un proceso para la sintesis de d-(17a)- 13-etil-17hidroxi -18, 19-dinorpregn -4-eno-20-ina -3-ona -oxima de alta pureza (ademas en norelgestromina) a traves de la acetilacion de d-norgestrel en la posicion 17, oximacion del grupo oxo en la posicion 3 del derivado de 17-acetoxi obtenido, y finalmente hidrolizacion del grupo acetoxi en la posicion 17 del derivado 3-oxima obtenido. El proceso de acuerdo a nuestra invencion es como sigue: la materia prima, d-(17a-17 -hidroxi-13 -etil-18, 19-dinor-pregn- 4-eno-20-ina -3ona (d-norgestrel) O pureza de 93-94% - se acetila con anhidrido acetico en acido acetico, en la presencia de cloruro de zinc y cloruro de hidrogeno, o acido perclorico al 70% en una atmosfera de gas inerte, y despues de la terminacion de la reaccion el exceso de anhidrido acetico y el derivado de Oacetato de enolO se descompone con acido hidroquiorico acuoso, luego el d-(17a)- 17acetoxi-13 -etil-18, 19-dinorpregn-4 -eno-20 -ina-3 -ona se aisla de la mezcla de reaccion a traves de la adicion de agua fria, el producto precipitado se filtra, se lava con agua, se seca, se disuelve en diclorometano o acetona y se clarifica con gel de silice u oxido de aluminio y carbon vegetal, despues de la filtracion del clarificador la solucion resultante se concentra y el residuo se recristaliza, el d-(17a) -17-acetoxi-13 -etil-18, 19-dinorpregn- 4-eno-20- ina-3 -ona obtenido de hace reaccionar ya sea con acetato de hidroxilamonio o con cloruro de hidroxilamonio en la presencia de acetato de sodio, en acido acetico en atmosfera de nitrogeno bajo agitacion vigorosa por aproximadamente 1 hora, despues de la terminacion de la reaccion se anade agua, el producto precipitado se filtra, se lava -17-acetoxi- 13-etil-18, 19-dinorpregn -4-eno-20 -ina-3-ona -oxima se hidroliza con una cantidad equivalente de un hidroxido de metal alcali en una solucion de alcano C1-C4, en atmosfera de nitrogeno entre una temperatura de aproximadamente 5-38 OC, bajo agitacion vigorosa, despues de la terminacion de la reaccion la mezcla se diluye con agua y el pH de la suspension resultante se ajusta a 7,5-9 con acido acetico, el producto precipitado se filtra, se lava con agua, se seca, el producto crudo se disuelve en etanol, se clarifica con carbon vegetal, y despues de la filtracion del clarificador se anade agua a la solucion obtenida, el d-(17a)- 17-acetoxi-13 -etil-18, 19-dinorpregn-4 -eno-20 -ina-3-ona -oxima de alta pureza precipitado se filtra, se lava con agua y en caso dado se recristaliza del etanol.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0301982A HUP0301982A2 (hu) | 2003-06-30 | 2003-06-30 | Eljárás nagy tisztaságú d-(17alfa)-13-etil-17-hidroxi-18,19-dinor-pregn-4-én-20-in-3-on-oxim előállítására |
| PCT/HU2004/000031 WO2005000868A1 (en) | 2003-06-30 | 2004-04-29 | Process for the synthesis of high purity d-(17alpha)-13-ethyl-17hydroxy-18,19-dinorpre:gn-4-ene-20-yne-3-one-oxime |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA05013948A true MXPA05013948A (es) | 2006-03-09 |
Family
ID=90001694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA05013948A MXPA05013948A (es) | 2003-06-30 | 2004-04-29 | Proceso para la sintesis de d-(17a)-13-etil-17-hidroxi-18 19-dinor-pregn-4-ene-20-ina-3-ona-oxima. |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP1638988B1 (es) |
| JP (1) | JP2007516946A (es) |
| CN (1) | CN100355771C (es) |
| AT (1) | ATE462712T1 (es) |
| AU (1) | AU2004251118A1 (es) |
| BR (1) | BRPI0412186A (es) |
| CA (1) | CA2528952A1 (es) |
| DE (1) | DE602004026306D1 (es) |
| EA (1) | EA008411B1 (es) |
| HR (1) | HRP20060038A2 (es) |
| HU (1) | HUP0301982A2 (es) |
| MX (1) | MXPA05013948A (es) |
| NO (1) | NO20060455L (es) |
| NZ (1) | NZ544378A (es) |
| RS (1) | RS20050897A (es) |
| UA (1) | UA80059C2 (es) |
| WO (1) | WO2005000868A1 (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7576226B2 (en) | 2003-06-30 | 2009-08-18 | Richter Gedeon Vegyeszeti Gyar Rt. | Process of making isomers of norelgestromin and methods using the same |
| ITMI20052464A1 (it) * | 2005-12-22 | 2007-06-23 | S N I F F Italia S P A | Procedimento per la preparazi9one di norelgestromin norelgestromina |
| CN108827950B (zh) * | 2018-05-31 | 2020-08-21 | 成都市科隆化学品有限公司 | 乙酸中微量乙酸酐的检测方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7306609A (es) * | 1972-05-26 | 1973-11-28 | ||
| US4027019A (en) * | 1975-07-24 | 1977-05-31 | Ortho Pharmaceutical Corporation | 3-Oximes of D-17α-ethynyl-19-nortestosterone esters and method |
| CN1188189C (zh) * | 1995-06-07 | 2005-02-09 | 奥瑟－麦内尔制药公司 | 基质层含有17－脱乙酰基诺孕酯的经皮贴片及基质的用途 |
-
2003
- 2003-06-30 HU HU0301982A patent/HUP0301982A2/hu unknown
-
2004
- 2004-04-29 UA UAA200600812A patent/UA80059C2/uk unknown
- 2004-04-29 DE DE602004026306T patent/DE602004026306D1/de not_active Expired - Fee Related
- 2004-04-29 NZ NZ544378A patent/NZ544378A/en unknown
- 2004-04-29 AU AU2004251118A patent/AU2004251118A1/en not_active Abandoned
- 2004-04-29 WO PCT/HU2004/000031 patent/WO2005000868A1/en active Application Filing
- 2004-04-29 JP JP2006518378A patent/JP2007516946A/ja active Pending
- 2004-04-29 CA CA002528952A patent/CA2528952A1/en not_active Abandoned
- 2004-04-29 BR BRPI0412186-4A patent/BRPI0412186A/pt not_active IP Right Cessation
- 2004-04-29 RS YUP-2005/0897A patent/RS20050897A/sr unknown
- 2004-04-29 EP EP04730316A patent/EP1638988B1/en not_active Expired - Lifetime
- 2004-04-29 MX MXPA05013948A patent/MXPA05013948A/es active IP Right Grant
- 2004-04-29 AT AT04730316T patent/ATE462712T1/de not_active IP Right Cessation
- 2004-04-29 EA EA200600119A patent/EA008411B1/ru not_active IP Right Cessation
- 2004-04-29 CN CNB2004800165780A patent/CN100355771C/zh not_active Expired - Fee Related
-
2006
- 2006-01-27 NO NO20060455A patent/NO20060455L/no not_active Application Discontinuation
- 2006-01-27 HR HR20060038A patent/HRP20060038A2/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2528952A1 (en) | 2005-01-06 |
| CN100355771C (zh) | 2007-12-19 |
| DE602004026306D1 (de) | 2010-05-12 |
| WO2005000868A1 (en) | 2005-01-06 |
| RS20050897A (sr) | 2007-08-03 |
| NO20060455L (no) | 2006-03-29 |
| EP1638988A1 (en) | 2006-03-29 |
| UA80059C2 (en) | 2007-08-10 |
| BRPI0412186A (pt) | 2006-08-22 |
| HUP0301982D0 (en) | 2003-09-29 |
| HRP20060038A2 (en) | 2006-11-30 |
| EA008411B1 (ru) | 2007-04-27 |
| CN1805970A (zh) | 2006-07-19 |
| AU2004251118A1 (en) | 2005-01-06 |
| NZ544378A (en) | 2008-02-29 |
| EP1638988B1 (en) | 2010-03-31 |
| ATE462712T1 (de) | 2010-04-15 |
| EA200600119A1 (ru) | 2006-06-30 |
| JP2007516946A (ja) | 2007-06-28 |
| HUP0301982A2 (hu) | 2005-04-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI256891B (en) | 17alpha-alkyl-17beta-oxy-estratrienes and intermediate products for their production, use of the 17alpha-alkyl-17beta-oxy-estratrienes for the production of pharmaceutical agents as well as pharmaceutical preparations | |
| HK1089444A1 (en) | Dihydropteridinones, method for the production and use thereof in the form of drugs | |
| CA2304713A1 (en) | Biphenyl-5-alkanoic acid derivatives and use thereof | |
| ZA976705B (en) | Process for the synthesis of protected esters of (S)-3,4-dihydroxybutric acid. | |
| UA84407C2 (en) | Acetyl 2-hydroxy-1,3 diaminoalkanes | |
| AU2003279624A1 (en) | Synthesis of estetrol via estrone derived steroids | |
| AU2001237347A1 (en) | Synthesis of 3,6-dialkyl-5,6-dihydro-4-hydroxy-pyran-2-one | |
| CA2333192A1 (en) | Synthesis of 3,6-dialkyl-5,6-dihydro-4-hydroxy-2h-pyran-2-one | |
| HUP0004731A2 (hu) | 2-Aril-benzo[b]tiofének alkalmazása ösztrogén elvonási szindróma kezelésére alkalmas gyógyszerkészítmények előállítására | |
| MXPA05013948A (es) | Proceso para la sintesis de d-(17a)-13-etil-17-hidroxi-18 19-dinor-pregn-4-ene-20-ina-3-ona-oxima. | |
| RS83104A (en) | Process to prepare eplerenone | |
| NO20023276L (no) | Fremgangsmåter fremstilling av betulinsyre | |
| WO2003038072A8 (en) | Generation and use of new types of dendritic cells | |
| AU2001272761A1 (en) | Sulfonic acid derivatives of hydroxamic acids and their use as medicinal products | |
| WO2002085921A3 (de) | Einfaches verfahren zur synthese von boswelliasäuren und derivaten davon | |
| MY138550A (en) | Method for synthesis of perindopril and its pharmaceutically acceptable salts | |
| BG105198A (en) | Process for the synthesis of (1h)-benzo[c]quinolizin-3-ones derivatives | |
| AU1382202A (en) | 17alpha fluoroalkyl steroids, method for producing the same and pharmaceutical compositions containing said compounds | |
| AU2003226287A1 (en) | Conversion of taxane molecules | |
| HUP0301332A2 (hu) | Új mono- és biszmetilén-szteroid-származékok és eljárás előállításukra és ezeket tartalmazó gyógyszerkészítmények | |
| BG108151A (en) | Caloporoside derivatives, methods for the production thereof and their use | |
| AU4757000A (en) | Method of producing methoxyimino acetic amide | |
| HUP0105347A2 (hu) | Eljárás indol-5-karbaldehidek előállítására | |
| AU2003221494A1 (en) | Process for the synthesis of pergolide | |
| AU4865201A (en) | An intermediate and process for its synthesis |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant or registration |