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 |
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Legal Events
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FG | Grant or registration |